臺灣博碩士論文加值系統

第一部份 中文摘要
在室溫下，利用碘(iodine)催化indole和pyrrol對nitroolefins進行Michael加成進而得到indolyl nitroalkane 5 和 pyrrolyl nitroalkane 7。相較於已知的路易士酸或貴重金屬當催化劑來說，此方法具有反應時間短及高產率的優點。

第二部份 中文摘要
在無溶劑的條件之下，利用碘 (iodine) 及2,4,6-trichloro﹝1,3,5﹞triazine (TCT) 加速醛 (aldehyde) 或酮 (ketone)、苯胺(aniline) 和亞磷酸三乙酯 (triethylphosphite)合成-胺基磷酸鹽類(-amino phosphonate)，此反應可在室溫或是60 oC條件下，以一鍋的方式進行反應得到高產率的產物。

第三部份 中文摘要
在室溫下，利用碘(iodine)催化醛、苯胺和acetylcyclohenxene以具有選擇性的特性，一鍋合成trans-endo-decahydroquinolin-4-one；此方法具有易操作、反應時間短、高產率、單一產物已及溫和的反應條件的優點。

第四部份 中文摘要
利用碘(iodine)催化醛和2-hydroxyacetophenone一鍋合成flavanone，此方法具有易操作、高產率、單一產物以及適用於各種官能基的優點。

第五部份 中文摘要
3-Amino chromans的衍生物在神經生物學及藥物學上，扮演極重要的腳色，因此發展有效率的合成方法為當務之急。我們利用salicylaldehyde 1 和nitromethane 經由 Knovenagel 反應路徑，接著走Michael 加成及aldol 的反應機構，在一鍋的條件下，合成出3-amino chromans的衍生物。

Part 1. I2-Catalyzed Michael Addition of Indole and Pyrrole to Nitroolefins 1

English Abstract 2

Chinese Abstract 3

Introduction 4

Result and Discussion 6

Conclusion 15

Experimental Section 16

General 16

Material 16

Procedure and NMR data 17

Reference 27

Spectrum Data and X-Ray Data 33




Part 2. Nonmetal Catalysts of Iodine and TCT Promote the One-pot Synthesis of Amino Phosphonates from Aldehydes or Ketones, Aniline, and Triethylphosphite Under Solvent
Free Conditions 87

English Abstract 88

Chinese Abstract 89

Introduction 90

Result and Discussion 93

Conclusion 101

Experimental Section 102

General 102

Material 102

Procedure and NMR data 103

Reference 118

Spectrum Data and X-Ray Data 124




Part 3. Stereoselective of Three-component Synthesis of trans-endo-decahydroquinolin-4-one Derivatives from Aldehydes, Aniline and Acetylcyclohexene 161

English Abstract 162

Chinese Abstract 163

Introduction 164

Result and Discussion 167

Conclusion 173

Experimental Section 174

General 174

Material 174

Procedure and NMR data 174

Reference 183

Spectrum Data and X-Ray Data 187





Part 4. One-Pot Synthesis of a Flavanone, Giving a Single Product in High Yield 291

English Abstract 292

Chinese Abstract 293

Introduction 294

Result and Discussion 296

Conclusion 303

Experimental Section 303

General 303

Material 304

Procedure and NMR data 304

Reference 309

Spectrum Data and X-Ray Data 315


Part 5. One-Pot Synthesis of 3-Nitrochroman 343

English Abstract 344

Chinese Abstract 345

Introduction 346

Result and Discussion 349

Conclusion 355

Experimental Section 355

General 355

Material 356

Procedure and NMR data 356

Reference 360

Spectrum Data and X-Ray Data 364

part 1 Reference

1. (a) Sundberg, R. J. The Chemistry of Indoles; Academic Press: New York, 1996, 113. (b) Livingstone, R. In Rodd ’s Chemistry of Carbon Compounds; Ansell, M. F., Ed.; Elsevier: Oxford, 1984; Vol. IV.
2. (a) Moore, R. E.; Cheuk, C.; Yang, X.-Q.; Patterson, G. M. L.; Bonjouklian, R.; Smitka, T. A.; Mynderse, J.: Foster, R. S.; Jones, N. D.; Swartzendruber, J. K.; Deeter, J. B. J. Org. Chem. 1987, 52, 1036. (b) Moore, R. E.; Cheuk, C.; Patterson, G. M. L. J. Am. Chem. Soc. 1984, 106, 6456. (c) Sakagami, M.; Muratake, H.; Natsume, M. Chem. Pharm. Bull. 1994, 42, 1393. (d) Fukuyama, T.; Chen, X. J. Am. Chem. Soc. 1994, 116, 3125.
3. Thomas, L. G. Heterocyclic Chemistry; Longman Press: England, 1997, Third Edition, Vol. XI, Part 1, 2 and 5.
4. (a) Jones, R. A.; Bean, G. P. The Chemistry of Pyrroles; Academic Press: London, 1977. (b) Lipshutz, B. H. Chem. Rev. 1986, 86, 795.
5. (a) Malcolm, M. C.; Nicholas, C.; Li, Z. Malcolm, S. Tetrahedron 1987, 43, 1117. (b) Iwata, S.; Ishiguro, Y.; Utsugi, M.; Mitsuhashi, K.; Tanaka, K. Bull. Chem. Soc. Jpn. 1993, 66, 2432. (c) Lounasmaa, M.; Tolvanen, A. Nat. Prod. Rep. 2000, 17, 75. (d) Joule, J. A. In Science of Synthesis, Vol. 10; Thomas, E. J., Ed.; Thieme: Stuttgart, 2000, 361. (e) Gribble, G. W. J. Chem. Soc., Perkin Trans. 1 2000, 1045. (f) Patterson, J. M.; Soedigdo, S. J. Org. Chem. 1968, 33, 2057. (g) Reinecke, M. G.; Johnson, H. M.; Sebastian, J. F. J. Am. Chem. Soc. 1963, 85, 2859.(h) Yadav, J. S.; Abraham, Sunny.; Reddy, B. V. S.; Sabitha, G. Tetrahedron Lett. 2001, 42, 8063. (i) Yadav, J. S.; Reddy, B. V. S.; Parimala, G. Synlett. 2002, 1143.
6. (a) Wang, S.-Y.; Ji, S.-J.; Loh, T.-P. Synlett. 2003, 2377. (b) Leonid, I.; Belen, K. Heterocycles. 1994, 37, 2029.
7. Arcadi, Antonio.; Bianchi, Gabriele.; Chiarini, Marco.;Anniballe, Gaetano D.; Marinelli, Fabio. Synlett. 2004, 944.
8. (a) Yadav, J. S.; Reddy, B. V. S.; Satheesh, G. Tetrahedron Lett. 2003, 44, 8331. (b) Yadav, J. S.; Reddy, B. V. S.; Abraham, S.; Sabitha, G. Synlett. 2002, 1550. (c) Harrington, P. E.; Kerr, M. A. Synlett. 1996, 11, 1047. (d) Agnusdei, M.; Bandini, M.; Melloni, A.; Umani-Ronchi, A. J. Org. Chem. 2003, 68, 7126. (e) Evans, D. A.; Scheidt, K. A.; Fandrik, K. R.; Wai Lam, H.; Wu, J. J. Am. Chem. Soc. 2003, 125, 10780. (f) Jørgensen, K. A. Synthesis. 2003, 1117. (g) Bandini, M.; Cozzi, P. G.; Giacobini, M.; Melchiorre, P.; Selva, S.; Umani-Ronchi, A. J. Org. Chem. 2002, 67, 3700. (h) Bandini, M.; Fagioli,M.; Melchiorre, P.; Melloni, A.; Umani-Ronchi, A. Tetrahedron Lett. 2003, 44, 5843. (i) Bandini, M.; Fagioli, M.; Melloni, A.; Umani-Ronchi, A. Synthesis. 2003, 397.
9. (a) Firouzabadi, H.; Iranpoor, N.; Nowrouzi, F. Chem.Commun. 2005, 789. (b) Loh, T. P.;Pei, J.; Lin, M. Chem. Commun. 1996, 20, 2315. (c) Babu, G.; Perumal, P. T. Aldrichim. Acta. 2000, 33, 16.(d) Loh, T. P.; Wei, L. L. Synlett. 1998, 975.
10. (a) Chakrabarty, M.; Basak, R.; Ghosh, N. Tetrahedron Lett. 2001, 41, 8331. (b) Komoto, I.; Kobayashi, S. Org. Lett. 2002, 4, 1115.
11. (a) Kim, K. M.; Ryu, E. K. Tetrahedron Lett. 1996, 37, 1441. (b) Firouzabadi, H.; Iranpoor, N.; Hazarkhani, H. J. Org. Chem. 2001, 66, 7527. (c) Firouzabadi, H.; Iranpoor, N.; Sobhani, S. Tetrahedron Lett. 2002, 43, 3653. (d) Yadav, J. S.; Reddy, B. V. S.; Reddy, M. S.; Prasad, A. R. Tetrahedron Lett. 2002, 43, 9703. (e) Bandgar, B. P.; Shaikh, K. A. Tetrahedron Lett. 2003, 44, 1959. (f) Saeeng, R.; Sirion, U.; Sahakitpichan, P.; Isobe, M. Tetrahedron Lett. 2003, 44, 6211. (j) Ji, S. J.; Wang, S. Y.; Zhang, Y.; Loh, T. P Tetrahedron. 2004, 60, 2051. (g) Yadav, J. S.; Reddy, B. V. S.; Shubashree, S.; Sadashiv, K. Tetrahedron Lett. 2004, 45, 2951. (h) Phukan, P. J. Org. Chem. 2004, 69, 4005. (i) Phukan, P. Tetrahedron Lett. 2004, 45, 4785. (j) Sun, J.; Dong, Y; Wang, X.; Wang, S.; Hu, Y. J. Org. Chem. 2004, 69, 8932. (k) Bhosale, R. S.; Bhosale, S. V.; Bhosale, S. V.; Wang, T.; Zubaidha, P. K. Tetrahedron Lett. 2004, 45, 9111. (l) Ke, B.; Qin, Y.; He, Q.; Huang, Z.; Wang, F. Tetrahedron Lett. 2005, 46, 1751. (m) Banik, B. K.; Fernandez, M.; Alvarez, C. Tetrahedron Lett. 2005, 45, 2479.
12. David, T.D. Aromatic Heterocyclic Chemistry; Oxford University Press: New York, 1992, Vol. XII of indole, Part 1, p.53.
13. (a) Rao, T. S.; Singth, A. K.; Trievdi, G. K. Heterycycles. 1984, 22, 1377. (b) Deshpande, S.; Mathur, H. H.;Trivedi, G. K. Synthesis. 1983, 835.
14. Booth, H.; Huckle, D.; Lockhart, I. M. J. Chem. Soc. Perkin Trans. 2. 1973, 2, 227.
15. Yao, C. F.; Yan, M. C.; Jang, Y. J. Tetrahedron Lett. 2001, 42, 2717.
16. (a) Noland, W. E. Org. Synth. 1964, 41, 67. (b) Ranganathan, D.; Rao, C. B.; Ranganathan, S.; Mehrotra, A. K.; Iyengar, R.; J. Org. Chem. 1980, 45, 1185. (c) Zimmerman, H. E.; Wang, P. J. Org. Chem. 2002, 67, 9216. (d) Flintoft, R. J.; Buzby, J. C.; Tucker, J. A. Tetrahedron Lett. 1999, 40, 4485. (e) Ranganathan, S.; Ranganathan, D.; Mehrotra, A. K. J. Am. Chem. Soc. 1974, 96, 5261.(f) Ranganathan, S.; Ranganathan, D.; Iyengar, R. Tetrahedron.1976, 32, 961. (g) Ranganathan, S.; Ranganathan, D.; Mehrotra, A. K. Synthesis. 1977, 289.
17. (a) Noland; Hartman. J. Am. Chem. Soc. 1954, 76, 3227. (b) Henry; Leete. J. Am. Chem. Soc.1957, 79, 5254. (c) Lyttle; Weisblat. J. Am. Chem. Soc. 1955, 77, 5747. (d) Hino, T.; Hasegawa, A.; Liu, J. J.; Nakagawa, M. Chem. Pharm. Bull. 1990, 38, 59-64. (e) Takeshita, M.; Yoshida, S.; Kohno, Y. Heterocycles, 1994, 37, 553. (f) Kruse, L. I.; Hilbert, E. L. Heterocycles. 1983, 37, 1373. (g) Hermkens, P. H. H.; Maarseveen, J. H. V.; Ottenheijm, H. C. J.; Kruse, C. G.; Scheeren, H. W. J. Org. Chem. 1990, 55, 3998. (h) Hermkens, P. H. H.; Maarseveen, J. H. V.; Ottenheijm, H. C. J.; Kruse, C. G.; Scheeren, H. W. Tetrahedron. 1990, 46, 833. (i) Somei, M.; Karasawa, Y.; Kaneko, C. Heterocycles. 1981, 16, 941. (j) Chikashita, H.; Morita, Y.; Itoh, K. Synth. Commun. 1985, 15, 527. (k) Liu, J.; Nakagawa, M.; Hino, T. Tetrahedron. 1989, 45, 7729. (l) Viaud, M. C.; Rollin, P. Tetrahedron Lett. 1990, 30, 1417. (m) Iwao, M.; Motol, O. Tetrahedron Lett. 1995, 36, 5929.




part 2 Reference

1. (a) Heaney, F. in Comprehensive Organic Functional Group Transformations, ed. Katritzky, A. R.; Meth-Cohn, O.; Rees, C. W. Elsevier Science, Oxford, 1995, vol. 4, ch. 4, 10. (b) Fields, E. K. J. Am. Chem. Soc., 1952, 74, 1528. (c) Fields, S.C. Tetrahedron 1999, 55, 12237. (d) Tyka, R. Tetrahedron Lett. 1970, 677. (e) Laschat, S.; Kunz, H. Synthesis 1992, 90. (f) Yuan, C.; Chen, S. Synthesis 1992, 1124. (g) Redmore, D. J. Org. Chem. 1978, 43, 992. (h) Afarinkia, K.; Cadogan, J. I. G.; Rees, C. W. Synlett. 1990, 415. (i) Huber, I. J. W.; Middlebrooks, M. Synthesis 1977, 883. (j) Birum, G. H. J. Org. Chem., 1974, 39, 209.
2. Kafarski, P.; Lejczak, B. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 63, 1993.
3. (a) Giannousis, P. P.; Bartlett, P. A. J. Med. Chem. 1987, 30, 1603. (b) Allen, M. C.; Fuhrer, W.; Tuck, B.; Wade, R.; Wood, J. M. J. Med. Chem. 1989, 32, 1652. (c) Parsons, W. H.; Patchett, A. A.; Bull, H. G.; Schoen, W. R.; Taub, D.; Davidson, J.; Combs, P. L.; Springer, J. P.; Gadesbusch, H.; Weissberger, B.; Valiant, M. E.; Mellin, T. N.; Busch, R. D. J. Med. Chem. 1988, 31, 1772.
4. (a) Atherton, F. R.; Hall, M. J.; Hassall, C. H.; Holmes, S. W.; Lambert, R. W.; Lloyd, W. J.; Ringrose, P. S. Antimicrob. Agents Chemother. 1980, 18, 897. (b) Atherton, F. R.; Hall, M. J.; Hassall, C. H.; Holmes, S. W.; Lambert, R. W.; Lloyd, W. J.; Nisbet, L. J.; Ringrose, P. S.; Westmacott, D. Antimicrob. Agents Chemother. 1981, 20, 470. (c) Atherton, F. R.; Hall, M. J.; Hassall, C. H.; Lambert, R. W.; Lloyd, W. J.; Ringrose, P. S.; Westmacott, D. Antimicrob. Agents Chemother. 1982, 22, 571. (d) Atherton, F. R.; Hassal, C. H.; Lambert, R. W. J. Med. Chem. 1986, 29, 29.
5. (a) Kukhar, V. P.; Hudson, H. R. In Aminophosphonic and Aminophosphinic Acids; John Wiley ＆ Sons: Chichester, 2000. (b) Gancarz, R.; Wieczorek, J. S. Synthesis 1978, 625. (c) Yuan, C.; Lim, C. Synthesis 1996, 507. (d) Yuan, C.; Zhao, L.; Yun, L.; Wang, H. Synthesis 2003, 887. (e) Seyferth, D.; Marmor, R. S.; Hilbert, P. J. Org. Chem. 1971, 36, 1379. (f) Worms, K. H.; Schmidt-Dunker, M. In Organic Phosphorus Compounds; Kosolapoff, G. M; Maier, L. Eds.; John Wiley ＆Sons: New York, 1976, Vol. 7. (g) Barycki, J.; Mastalers, P. Tetrahedron Lett. 1970, 36, 3147. (h) Chakraborty, S.; Engel, R. Synth. Commun. 1991, 21, 1039. (i) Manabe, K.; Kobayashi, S. Chem. Commun. 2000, 669. (j) Maury, C.; Wang, Q.; Gharbaoui, T.; Chiadmi, M.; Tomas, A.; Royer, J.; Husson, H. P. Tetrahedron 1997, 53, 3267. (k) Vercruysse-Moreira, K.; Dejugnat, C.; Etemad-Moghadam. G. Tetrahedron 2002, 58, 5651. (l) Kukhar, V. P.; Solodenjo, V. A.; Russ. Chem. Rev. (Engl. Transl.) 1978, 56, 859. (m) Laschat, S.; Kunz, H. Synthesis 1992, 90. (n) Yokomatsu, T.; Yoshida, Y.; Shibuya, S. J. Org. Chem. 1994, 59, 7930.
6. Zon, J. Pol. J. Chem. 1981, 55, 643.
7. Qian, C.; Huang, T. J. Org. Chem. 1998, 63, 4125.
8. Ranu, B. C.; Hajra, A.; Jana, U. Org. Lett. 1999, 1, 1141.
9. Shen, Q.; Fan, X.; Luo, Y.; Deng, M. Eur. J. Org. Chem. 2003, 4278.
10. Lee, S.; Park, T. S.; Kang, J.; Lee, J. K. Chem. Commun. 2001, 1698.
11. (a) Kim, K. M.; Ryu, E. K. Tetrahedron Lett. 1996, 37, 1441. (b) Firouzabadi, H.; Iranpoor, N.; Hazarkhani, H. J. Org. Chem. 2001, 66, 7527. (c) Firouzabadi, H.; Iranpoor, N.; Sobhani, S. Tetrahedron Lett. 2002, 43, 3653. (d) Yadav, J. S.; Reddy, B. V. S.; Reddy, M. S.; Prasad, A. R. Tetrahedron Lett. 2002, 43, 9703. (e) Bandgar, B. P.; Shaikh, K. A. Tetrahedron Lett. 2003, 44, 1959. (f) Saeeng, R.; Sirion, U.; Sahakitpichan, P.; Isobe, M. Tetrahedron Lett. 2003, 44, 6211. (g) Yadav, J. S.; Reddy, B. V. S.; Shubashree, S.; Sadashiv, K. Tetrahedron Lett. 2004, 45, 2951. (h) Phukan, P. J. Org. Chem. 2004, 69, 4005. (i) Phukan, P. Tetrahedron Lett. 2004, 45, 4785. (j) Sun, J.; Dong, Y; Wang, X.; Wang, S.; Hu, Y. J. Org. Chem. 2004, 69, 8932. (k) Bhosale, R. S.; Bhosale, S. V.; Bhosale, S. V.; Wang, T.; Zubaidha, P. K. Tetrahedron Lett. 2004, 45, 9111. (l) Ke, B.; Qin, Y.; He, Q.; Huang, Z.; Wang, F. Tetrahedron Lett. 2005, 46, 1751. (m) Banik, B. K.; Fernandez, M.; Alvarez, C. Tetrahedron Lett. 2005, 45, 2479. (n) Chu, C.-M.; Gao, S.; Sastry, M. N. V.; Yao, C.-F. Tetrahedron Lett, 2005, 46, 4971. (o) Ko, S.; Sastry, M. N. V.; Lin, C.; Yao, C.-F. Tetrahedron Lett, 2005, 46, 5771. (p) Shivaji, V. M.; Sastry, M. N. V.; Wang, C.-C.; Yao, C.-F. Tetrahedron Lett. 2005, 46, 6345. (q) Lin, C.; Hsu, J.; Sastry, M. N. V.; Fang, H.; Tu, Z.; Liu, J.-T.; Yao, C.-F. Tetrahedron 2005, 61, 11751. (r) Ko, S.; Lin, C.; Tu, Zhijay,; Wang, Y.-F.; Wang, C.-C.; Yao, C.-F. Tetrahedron Lett. 2006, 47, 487. (s) Gao, S.; Tzeng, T.; Sastry, M. N. V.; Chu, C.-M.; Liu, J.-T.; Lin, C.; Yao, C.-F. Tetrahedron Lett. 2006, 47, 1889.
12. (a) Rayle, H. L.; Fellmeth, L. Org. Proc. Res. Dev. 1999, 3, 172 and references cited therein. (b) Kaminski, Z. J.; Paneth, P.; Rudzinski, J. J. Org. Chem. 1998, 63, 4248. (c) Falchi, A.; Giacomelli, G.; Porcheddu, A.; Taddei, M. Synlett. 2000, 275. (d) Falorni, M.; Giacomelli, G.; Porcheddu, A.; Taddei, M. J. Org. Chem. 1999, 64, 8962. (e) Kaminska, J. E.; Kaminski, Z. J.; Gora, J. Synthesis 1999, 4, 593. (f) Kaminski, Z. J.; Koleginska, B.; Markowicz, S. W.; Pokrzeptowicz, K. Polish J. Chem. 1999, 73, 1965.
13. Chandrasekhar, S.; Prakash, S. J.; Jagadeshwar, V.; Narsihmulu, Ch. Tetrahedron Lett. 2001, 42, 5561.
14. Yadav, J. S.; Reddy, B. V. S.; Madan, Ch. Synlett. 2001, 1131.




part 3 Reference

1. Kornienko, A.; Evdokimov, N. M.; Magedov, I. V.; Kireev, A. S. Organic Lett. asap.
2. (a) Ramo´n, D. J.; Miguel, Y. Angew. Chem. Int. Ed. 2005, 44, 1602. (b) Orru, R. V. A.; de Greef, M. Synthesis 2003, 1471. (c) Ugi, I.; Heck, S. Comb. Chem. High Throughput Screening 2001, 4, 1. (d) Weber, L.; Illgen, K.; Almstetter, M. Synlett 1999, 366.
3. (a) Tietze, L. F.; Kettschau, G. Top. Curr. Chem. 1997, 189, 1. (b) Buonora, P.; Olsen, J.-C.; Oh, T. Tetrahedron 2001, 57, 6099. (c) Jørgensen, K. A. Angew. Chem., Int. Ed. 2000, 39, 3559. (d) Kobayashi, S.; Komiyama, S.; Ishitani, H. Angew. Chem., Int. Ed. 1998, 37, 979. (e) Bromidge, S.; Wilson, P. C.; Whiting, H. Tetrahedron Lett. 1998, 39, 8905. (f) Jorgensen, K. A.; Hazell, R. G.; Johansen, M.; Yao, S. Angew. Chem., Int. Ed. 1998, 37, 3121. (g) Jorgensen, K. A.; Hazell, R. G.; Audrain, H.; Johansen, M.; Yao, S. J. Am. Chem. Soc. 1998, 120, 8599. (h) Kobayashi, S.; Kusakabe, K.-I.; Komiyama, S.; Ishitani, H. J. Org. Chem. 1999, 64, 4220. (i) Jorgensen, K. A.; Hazell, R. G.; Saaby, S.; Yao, S. Chem. Eur. J. 2000, 6, 2435.
4. (a) Le Coz, L.; Veyrat-Martin, C.; Wartsky, L.; Seyden-Penne, J.; Bois, C.; Philoche-Levisalles, M. J. Org. Chem. 1990, 55, 4870. (b) Nogue , D.; Paugam, R.; Wartski, L. Tetrahedron Lett. 1992, 33, 1265. (c) Paugam, R.; Wartski, L. Tetrahedron Lett. 1991, 32, 491. (d) Paugam, R.; Valenciennes, E.; Coz-Bardol, L. L.; Garde, J-C.; Wartski, L.; Lance, M.; Nierlich, M. Tetrahedron Asymm. 2000, 11, 2509.
5. (a) Kim, K. M.; Ryu, E. K. Tetrahedron Lett. 1996, 37, 1441. (b) Firouzabadi, H.; Iranpoor, N.; Hazarkhani, H. J. Org. Chem. 2001, 66, 7527. (c) Firouzabadi, H.; Iranpoor, N.; Sobhani, S. Tetrahedron Lett. 2002, 43, 3653. (d) Yadav, J. S.; Reddy, B. V. S.; Reddy, M. S.; Prasad, A. R. Tetrahedron Lett. 2002, 43, 9703. (e) Bandgar, B. P.; Shaikh, K. A. Tetrahedron Lett. 2003, 44, 1959. (f) Saeeng, R.; Sirion, U.; Sahakitpichan, P.; Isobe, M. Tetrahedron Lett. 2003, 44, 6211. (g) Yadav, J. S.; Reddy, B. V. S.; Shubashree, S.; Sadashiv, K. Tetrahedron Lett. 2004, 45, 2951. (h) Phukan, P. J. Org. Chem. 2004, 69, 4005. (i) Phukan, P. Tetrahedron Lett. 2004, 45, 4785. (j) Sun, J.; Dong, Y; Wang, X.; Wang, S.; Hu, Y. J. Org. Chem. 2004, 69, 8932. (k) Bhosale, R. S.; Bhosale, S. V.; Bhosale, S. V.; Wang, T.; Zubaidha, P. K. Tetrahedron Lett. 2004, 45, 9111. (l) Ke, B.; Qin, Y.; He, Q.; Huang, Z.; Wang, F. Tetrahedron Lett. 2005, 46, 1751. (m) Banik, B. K.; Fernandez, M.; Alvarez, C. Tetrahedron Lett. 2005, 45, 2479. (n) Chu, C.-M.; Gao, S.; Sastry, M. N. V.; Yao, C.-F. Tetrahedron Lett, 2005, 46, 4971. (o) Ko, S.; Sastry, M. N. V.; Lin, C.; Yao, C.-F. Tetrahedron Lett, 2005, 46, 5771. (p) Shivaji, V. M.; Sastry, M. N. V.; Wang, C.-C.; Yao, C.-F. Tetrahedron Lett. 2005, 46, 6345. (q) Lin, C.; Hsu, J.; Sastry, M. N. V.; Fang, H.; Tu, Z.; Liu, J.-T.; Yao, C.-F. Tetrahedron 2005, 61, 11751. (r) Ko, S.; Lin, C.; Tu, Zhijay,; Wang, Y.-F.; Wang, C.-C.; Yao, C.-F. Tetrahedron Lett. 2006, 47, 487. (s) Gao, S.; Tzeng, T.; Sastry, M. N. V.; Chu, C.-M.; Liu, J.-T.; Lin, C.; Yao, C.-F. Tetrahedron Lett. 2006, 47, 1889.
6. Monnereau, C.; Blart, E.; Odobel, F. Tetrahedron 2005, 46, 5421.
7. Babu, G.; Perumal, P. T. Tetrahedron 1998, 54, 1627.



part 4 Reference

1. (a) Khattab, A. M.; Grace, M. H.; El-Khrisy, E. A. Pharmazie 2001, 56, 661; (b) Horie, T.; Tominaga, H.; Kawamura, Y.; Hada, T.; Ueda, N.; Amano, Y.; Yamamoto, S. J. Med.Chem. 1991, 34, 2169; (c) van Acker, F. A. A.; Hageman, J. A.; Haenen, G. R. M. M.; van der Vijgh, W. J. F.; Bast, A.; Menge, W. M. P. B. J. Med. Chem. 2000, 43, 3752; (d) Nussbaumer, P.; Lehr, P.; Billich, A. J. Med. Chem. 2002, 45, 4310; (e) Souza, J.; Molfetta, J. F. A.; Honorio, K. M.; Santos, R. H. A.; Silva, A. B. F. J. Chem. Inf. Comput. Sci. 2004, 44, 1153; (f) Zhou, Z.; Zhao, P.; Huang, W.; Yang, G. Adv. Synth. Catal. 2006, 348, 63.
2. (a) Ferrali, M.; Donati, D.; Bambagioni, S.; Fontani, M.; Giorgi, G.; Pietrangelo, A. Bioorg. Med. Chem. 2001, 9, 3041; (b) Lipinski, C. A.; Aldinger, C. E.; Beyer, T. A.; Bordner, J.; Burdi, D. F.; Bussolotti, D. L.; Inskeep, P. B.; Siegel, T. W. J. Med, Chem. 1992, 35, 2169; (c) Ankhiwala, M. D. J.Indian Chem.Soc. 1990, 67, 913. (d) Pouget, C.; Fagnere, C.; Basly, J-P.; Habrioux, G.; Chulia, A-J. Bioorg.Med. Chem.Lett. 2002, 12, 1059– 1061. (e) Hsieh, H. K.; Lee, T. H.; Wang, J. P.; Wang, J. J.; Lin, C. N. Pharm.Res. 1998, 15, 39.
3. (a) Dhar, D. N. The Chemistry of Chalcone and Related Compounds; Cambridge University Press: London, 1973; (b) Reichel, L.; Proksch, G. Liebigs Ann. Chem. 1971, 745, 59; (c) Nabaei-Bidhendi, G.; Bannerjee, N. R. J. Indian Chem. Soc. 1990, 67, 43; (d) Brennan, C. M.; Hunt, I.; Jarvis, T. C.; Johnson, C. D.; McDonnell, P. D. Can. J. Chem. 1990, 68, 1780; (e) Wurm, G.; Schnetzer, D. Arch. Pharm. (Weinheim) 1992, 325, 717; (f) Chaturvedi, R.; Patil, P. N.; Mulchandani, N. B. Indian J. Chem. 1992, 31B, 340–341. (g) Cheng, P. L.; Fournari, P.; Tirouflet, J. Bull. Soc. Chim. Fr. 1963, 2248.
4. (a) Keane, D. D.; Marathe, K. G.; O_Sullivan, W. I.; Philbin, E. M.; Simons, R. M.; Teague, P. C. J. Org. Chem. 1970, 35, 2286; (b) Reichel, L.; Weber, F. G. Pharmazie 1975, 30, 195; (c) Dutta, C. P.; Roy, L. P. K. Indian J. Chem. 1975, 13, 425; (d) Patonay, T.; Litkei, G.; Zsuga, M.; Kiss, A. Org. Prep. Proced. Int. 1984, 16, 315; (e) Thomsen, I.; Torssell, B. G. Acta Chem. Scand. Ser. B 1988, 42, 303; (f) Climent, M. J.; Garcia, H.; Iborra, S.; Miranda, M. A.; Primo, J. Hetrocycles 1989, 29, 115; (g) Bagade, M. B.; Thool, A. W.; Lokhande, P. D.; Ghiya, B. J. Indian J. Chem. 1991, 30B, 973; (h) Chandrasekhar, S.; Vijeender, K.; Reddy, K. V. Tetrahedron Lett. 2005, 46, 6991.
5. Sangawan, N. K.; Varma, B. S.; Dhindsa, K. S. Chem. Ind. (London) 1984, 271.
6. (a) Harris, T. M.; Carney, R. L. J. Am. Chem. Soc. 1967, 89, 6734; (b) Hoshino, Y.; Takeno, N. Bull. Chem. Soc. Jpn. 1986, 59, 2903.
7. (a) Stermitz, F. R.; Adamovics, J. A.; Geigert, J. Tetrahedron 1975, 31, 1593; (b) Matsushima, R.; Kageyama, H. J. Chem. Soc., Perkin Trans. 2 1985, 743; (c) Pandey, G.; Krishna, A.; Kumaraswamy, G. Tetrahedron Lett. 1987, 28, 4615; (d) Maki, Y.; Shimada, K.; Sako, M.; Hirota, K. Tetrahedron 1988, 44, 3187.
8. Sanicanin, Z.; Tabakovic, I. Tetrahedron Lett. 1986, 27, 407.
9. Ali, S. M.; Iqbal, J.; Ilyas, M. J. Chem. Res. (S) 1984, 236.
10. (a) Chen, H. Y.; Dykstra, K. D.; Birzin, E. T.; Frisch, K.; Chan, W.; Yang, Y. T.; Mosley, R. T.; DiNinno, F.; Rohrer, S. P.; Schaeffer, J. M.; Hammond, M. L. J. Bioorg. Med. Chem. Lett. 2004, 14, 1417; (b) Choudary, B. M.; Ranganath, K. V. S.; Yadav, J.; Kantam, M. L. Tetrahedron Lett. 2005, 46, 1369; (c) Dauzonne, D.; Monneret, C. Synthesis 1997, 1305; (d) Dauzonne, D.; Demerseman, P. Synthesis 1990, 66; (e) Dauzonne, D.; Grandjean, C. Synthesis 1992, 677. (f) Chandrasekhar, S.; Vijeender, K.; Reddy, K. V. Tetrahedron Lett. 2005, 46, 6991.
11. (a) Bhatia, V. K.; Krishnamurthy, H. G.; Madhav, R.; Seshadri, T. R. Tetrahedron Lett. 1968, 3859; (b) Flammang, M.; Frederic, D.; Wermuth, C. G. C. R. Hebd. Seances Acad. Sci., Ser. C 1978, 286, 721; (c) Jyotsna, D.; Rao, A. V. S. Indian J. Chem. 1987, 26B, 877; (d) Izumi, T.; Hino, T.; Kasahara, A. J. Chem. Soc., Perkin Trans. 1 1992, 1265; (e) Sing, O. V. Org. Prep. Proced. Int. 1993, 25, 693.
12. Joglekar, S. J.; Samant, S. D. Tetrahedron Lett. 1988, 29, 241.
13. Subramanian, R. S.; Balasubramanian, K. K. J. Chem. Soc., Chem. Commun. 1990, 1469.
14.Hoshino, Y.; Takeno, N. Bull. Chem. Soc. Jpn. 1986, 59, 2903.
15. (a) Kim, K. M.; Ryu, E. K. Tetrahedron Lett. 1996, 37, 1441. (b) Firouzabadi, H.; Iranpoor, N.; Hazarkhani, H. J. Org. Chem. 2001, 66, 7527. (c) Firouzabadi, H.; Iranpoor, N.; Sobhani, S. Tetrahedron Lett. 2002, 43, 3653. (d) Yadav, J. S.; Reddy, B. V. S.; Reddy, M. S.; Prasad, A. R. Tetrahedron Lett. 2002, 43, 9703. (e) Bandgar, B. P.; Shaikh, K. A. Tetrahedron Lett. 2003, 44, 1959. (f) Saeeng, R.; Sirion, U.; Sahakitpichan, P.; Isobe, M. Tetrahedron Lett. 2003, 44, 6211. (g) Yadav, J. S.; Reddy, B. V. S.; Shubashree, S.; Sadashiv, K. Tetrahedron Lett. 2004, 45, 2951. (h) Phukan, P. J. Org. Chem. 2004, 69, 4005. (i) Phukan, P. Tetrahedron Lett. 2004, 45, 4785. (j) Sun, J.; Dong, Y; Wang, X.; Wang, S.; Hu, Y. J. Org. Chem. 2004, 69, 8932. (k) Bhosale, R. S.; Bhosale, S. V.; Bhosale, S. V.; Wang, T.; Zubaidha, P. K. Tetrahedron Lett. 2004, 45, 9111. (l) Ke, B.; Qin, Y.; He, Q.; Huang, Z.; Wang, F. Tetrahedron Lett. 2005, 46, 1751. (m) Banik, B. K.; Fernandez, M.; Alvarez, C. Tetrahedron Lett. 2005, 45, 2479. (n) Chu, C.-M.; Gao, S.; Sastry, M. N. V.; Yao, C.-F. Tetrahedron Lett, 2005, 46, 4971. (o) Ko, S.; Sastry, M. N. V.; Lin, C.; Yao, C.-F. Tetrahedron Lett, 2005, 46, 5771. (p) Shivaji, V. M.; Sastry, M. N. V.; Wang, C.-C.; Yao, C.-F. Tetrahedron Lett. 2005, 46, 6345. (q) Lin, C.; Hsu, J.; Sastry, M. N. V.; Fang, H.; Tu, Z.; Liu, J.-T.; Yao, C.-F. Tetrahedron 2005, 61, 11751. (r) Ko, S.; Lin, C.; Tu, Zhijay,; Wang, Y.-F.; Wang, C.-C.; Yao, C.-F. Tetrahedron Lett. 2006, 47, 487. (s) Gao, S.; Tzeng, T.; Sastry, M. N. V.; Chu, C.-M.; Liu, J.-T.; Lin, C.; Yao, C.-F. Tetrahedron Lett. 2006, 47, 1889.




part 5 Reference

1. (a) Yasunaga, T.; Naito, R.; Kontani, T.; Tsukamoto, S.; Nomura, T.; Yamaguchi, T.;Mase, T. J. Med. Chem. 1997, 40, 1252. (b) Butler, T. W.; Blake, J. F.; Bordner, J.; Butler, P.; Chenard, B. L.; Collins, M. A.; DeCosta, D.; Ducat, M. J.; Eisenhard, M. E.; Menniti, F. S.; Pagnozzi, M. J.; Sands, S. B.; Segelstein, B. E.; Volberg, W.; White, W. F.; Zhao, D. J. Med. Chem. 1998, 41, 1172. (c) Reddy, K. A.; Lohray, B. B.; Bhushan, V.; Reddy, A. S.; Mamidi, N. V. S. R.; Reddy, P. P.; Saibaba, V.; Reddy, N. J.; Suryaprakash, A.; Misra, P.; Vikramadithyan, R. K.; Rajagopalan, R. J. Med. Chem. 1999, 42, 3265. (d) Efange, S. M. N.; Tu, Z.; Hohenberg, K. V.; Francesconi, L.; Howell, R. C.; Rampersad, M. V.; Todaro, L. J.; Papke, R. L.; Kung, M. J. Med. Chem. 2001, 44, 4704.
2. Zafra-Polo, M. C.; Gonzalez, M. C.; Tormo, J. R.; Estornell, E.; Cortes, D. J. Nat. Prod. 1996, 59, 913.
3. Ogundaini, A.; Farah, M.; Perera, P. J. Nat. Prod. 1996, 59, 587.
4. (a) Rezaie, R.; Joseph, B.; bremmner, J. B.; Delagrsnce, P.; Kopp, C.; Adam, G.; Guardiola-Lemaitre, B. J. Med. Chem. 1996, 39, 4285. (b) Johansson, A. M.; Holmberg, P.; Sohn, D.; Leideborg, R.; Caldirola, P.; Zlatoidsky, P.; Hanson, S.; Mohell, N.; Rosqvist, S.; Nordvall, G.; Johansson, R. J. Med. Chem. 2004, 47, 3927. (c) Pave, G.; Usse-Versluys, S.; Viaud-Massuard, M.-C.; Guillaumet, G. Organic Lett. 2003, 5, 4253. (d) Pave, G.; Leger, J.-M.; Jarry, C.; Viaud-Massuard, M.-C.; Guillaumet, G. J. Org. Chem. 2003, 68, 1401. (e) Linnanen, T.; Brisander, M.; Unelius, L.; Sundholm, G.; Hacksell, U.; Johansson, A. M. J. Med. Chem. 2000, 43, 1339.
5. (a) Simth, L. I.; Ungnade, E.; Hoehn, H. H.; Wawzonek, S. J. Org. Chem. 1939, 4, 311. (b) Merten, R.; Muller, G. Chem. Ber. 1964, 97, 682. (c) Clark, E. R.; William, S. G. J. Chem. Soc. (B) 1967, 859. (d) Cohen, N.; Lopresti, J.; Neukom, C. J. Org. Chem. 1981, 46, 2445. (e) Bigi, F.; Carloni, S.; Maggi, R.; Muchetti, C.; Sartori, G. J. Org. Chem. 1997, 62, 7024. (f) Kaye, P. T.; Robinson, R. S. Synth. Commun. 1996, 26, 2085. (g) Kaye, P. T.; Nocanda, X. W. J. Chem. Soc., Perkin Trans. 1 2000, 1331.
6. (a) Normant, H.; Maitte, P. C. R. Hebd. Seances. Acad. Sci. 1952, 234, 1787. (b) Parham,W. E.; Jones, L. D.; Sayed, Y. A. J. Org. Chem. 1976, 41, 1184. (c) Zhao, Q.; Han, F.; Romero, D. L. J. Org. Chem. 2002, 67, 3317.
7. (a) Vida, J. A.; Gut, M. J. Org. Chem. 1968, 33, 1202. (b) Schweizer, E. E.; Berninger, C. J.; Crouse, D. M.; Davis, R. A.; Logothetis, R. S. J. Org. Chem. 1969, 34, 207. (c) Hepworth, J. D.; Jones, T. K.; Livingstone, R. Tetrahedron 1981, 37, 2613. (d) Brisander, M.; Caldirola, P.; Johansson, A. M.; Hacksell, U. J. Org. Chem. 1998, 63, 5362.
8. (a) Bolon, D. A. J. Org. Chem. 1970, 35, 3666. (b) Chambers, J. D.; Crawford, J.; Williams, H. W. R.; Dufresne, C.; Scheigetz, J.; Bernstein, M. A.; Lau, C. K. Can. J. Chem. 1992, 70, 1717. (c) Jones, R. M.; Selenski, C.; Pettus, P. R. R. J. Org. Chem. 2002, 67, 6911. (d) Nonland, W. E.; Kedrowski, B. L. J. Org. Chem. 2002, 67, 8366.
9. (a) Rene, L.; Royer, R. Eur. J. Med. Chem. Chim. Ther. 1975, 10, 72. (b) Sakakibara, T.; Koezuka, M.; Sudoh, R. Bull. Chem. Soc. Jpn. 1978, 51, 3095. (c) Rao, T. S.; Deshpande, S.; Mathur, H. H.; Trivedi, G. K. Heterocycles 1984, 22, 1943. (d) Varma, R. S.; Kabalka, G. W. Heterocycles 1985, 23, 139. (e) Varma, R. S.; Kadkhodayan, M.; Kabalka, G. W. Synthesis 1986, 486. (f) Varma, R. S.; Kadkhodayan,M.; Kabalka, G. W. Heterocycles 1986, 24, 1647. (g) Yan, M.-C.; Jang, Y.-J.; Yao, C.-F. Tetrahedron Lett. 2001, 42, 2717. (h) Yan, M.-C.; Jang, Y.-J.; Kuo, W.-Y.; Tu, Z.; Shen, K.-H.; Cuo, T.-S.; Ueng, C.-H.; Yao, C.-F. Heterocycles 2002, 57, 1033
10. (a) Hammarberg, E.; Nordvall, G.; Leideborg, R.; Nylo¨f, M.; Hanson, S.; Johansson, L.; Thorberg, S.-O.; Tolf, B.-O.; Jerning, E.; Svantesson, G. T.; Mohell, N.; Ahlgren, C.; Westlind-Danielsson, A.; Cso¨regh, I.; Johansson, R. J. Med. Chem. 2000, 43, 2837. (b) Dupau, P.; Le Gendre, P.; Bruneau, C.; Dixneuf, P. H. Synlett 1999, 11, 1832. (c) Dupau, P.; Bruneau, C.; Dixneuf, P. H. Tetrahedron: Asymmetry 1999, 10, 3467. (d) See Supporting Information and also: (e) Garner, P.; Park, J. M. Org. Synth. 1992, 70, 18. (f) Dondoni, A.; Perrone, D. Synthesis 1997, 5, 527. (g) Curran, D. P. In ComprehensiVe Organic Synthesis; Pergamon Press: Elmsford, NY, 1991; Vol. 4, pp 715-831. (h) Usse, S.; Guillaumet, G.; Viaud, M. C. J. Org. Chem. 2000, 65, 914. (i) Usse, S.; Pave´, G.; Guillaumet, G.; Viaud-Massuard, M.-C. Tetrahedron: Asymmetry 2001, 12, 1689. (j) Husson, H.-P.; Royer, J. J. Chem. Soc. Rev. 1999, 28, 383 and references therein. (k) Bonin, M.; Grierson, D. S.; Royer, J.; Husson, H.-P. Org. Synth. 1992, 70, 54.