Reaction of the Morita-Baylis-Hillman acetates of 2-azidobenzaldehydes with triethyl phosphite: Synthesis of 1-diethylphosphono-1,2-dihydroquinolines and 3-acetoxymethylquinolines

Synthesis

Volumn , Issue 12, 2006, Pages 1953-1960

  Yi, Hyung Woo ^a   Park, Hyun Woo ^a   Song, Young Seok ^a   Lee, Kee Jung ^a  

^a Hanyang University   (South Korea)

Author keywords

Iminophosphorane; Michaelis Arbuzov rearrangement; Morita Baylis Hillman acetate; Quinoline; Triethyl phosphite

Indexed keywords

CHEMICAL REACTIONS; PARAFFINS; PHOSPHORUS COMPOUNDS; SYNTHESIS (CHEMICAL);

IMINOPHOSPHORANE; MICHAELIS-ARBUZOV REARRANGEMENT; MORITA-BAYLIS-HILLMAN ACETATE; QUINOLINE; TRIETHYL PHOSPHITE;

ALDEHYDES;

1 DIETHYLPHOSPHONO 1,2 DIHYDROQUINOLINE DERIVATIVE; 2 AZIDOBENZALDEHYDE DERIVATIVE; 2 METHOXY 6 NITRO 3 PROPANOYLOXYMETHYLQUINOLINE; 3 ACETOXYMETHYL 2 METHOXY 6 NITROQUINOLINE; 3 ACETOXYMETHYL 2 METHOXYQUINOLINE; 3 ACETOXYMETHYL 2 METHYL 6 NITROQUINOLINE; 3 ACETOXYMETHYL 2 METHYLQUINOLINE; 3 ACETOXYMETHYL 6 METHYL 2 METHYLQUINOLINE; 3 ACETOXYMETHYLQUINOLINE DERIVATIVE; 3 CARBOMETHOXY 1 DIETHYLPHOSPHONO 1,2 DIHYDROQUINOLINE; 3 CARBOMETHOXY 1 DIETHYLPHOSPHONO 6 METHOXY 1,2 DIHYDROQUINOLINE; 3 CARBOMETHOXY 1 DIETHYLPHOSPHONO 6 NITRO 1,2 DIHYDROQUINOLINE; 3 CYANO 1 DIETHYLPHOSPHONO 1,2 DIHYDROQUINOLINE; 3 CYANO 1 DIETHYLPHOSPHONO 6 METHOXY 1,2 DIHYDROQUINOLINE; 3 CYANO 1 DIETHYLPHOSPHONO 6 NITRO 1,2 DIHYDROQUINOLINE; 3 HYDROXYMETHYL 2 METHOXY 6 NITROQUINOLINE; ACETIC ACID DERIVATIVE; BENZALDEHYDE DERIVATIVE; METHYL 3 (2 AZIDO 5 NITROPHENYL) 2 METHYLENE 3 PROPANOYLOXYPROPANOATE; METHYL 3 ACETOXY 3 (5 NITRO 2 TRIETHOXYIMINOPHOSPHORANYLIDENE)PHENYL 2 METHYLENEPROPANOATE; PHOSPHITE; QUINOLINE DERIVATIVE; TRIETHYL PHOSPHITE; UNCLASSIFIED DRUG;

ARTICLE; BAYLIS HILLMAN REACTION; DRUG SYNTHESIS;

EID: 33745741434     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-942383     Document Type: Article

References (57)

1. (a) Michael, J. P. Nat. Prod. Rep. 1997, 14, 605.
2. (b) Balasubramanian, M.; Keay, J. G. In Comprehensive Heterocyclic Chemistry II, Vol. 5; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996, 245-300.
3. (c) Jones, G. In Comprehensive Heterocyclic Chemistry II, Vol. 5; Katritzky, A. R.; Rees, C. W.; Screven, E. F. V., Eds.; Pergamon: Oxford, 1996, 167-243.
4. (a) Tetsuya, A.; Takayuki, D.; Koji, F. Jpn. Patent, 04282370,1992; Chem. Abstr. 1993, 118, 147472u.
5. (b) Uchida, M.; Chihiro, M.; Morita, S.; Yamashita, H.; Yamasaki, K.; Kanbe, T.; Yabuuchi, Y.; Nakagawa, K. Chem. Pharm. Bull. 1990, 38, 534.
6. (c) Epstein, S. S.; Saporoschetz, I. B.; Small, M.; Park, W.; Mantel, N. Nature (London) 1965, 208, 655.
7. (a) Engler, T. A.; Lynch, K. O. Jr.; Chai, W.; Meduna, S. P. Tetrahedron Lett. 1995, 36, 2713.
8. (b) Engler, T. A.; La Tessa, K. O.; Iyenger, R.; Chai, W.; Agrios, K. Bioorg. Med. Chem. 1996, 4, 1755.
9. (a) Yavari, I.; Ramazani, A.; Esmaili, A. A. J. Chem. Res., Synop. 1997, 208.
10. (b) Williamson, N. M.; March, D. R.; Ward, A. D. Tetrahedron Lett. 1995, 36, 7721.
11. (c) Kobayashi, K.; Nakahashi, R.; Shimizu, A.; Kitamura, T.; Morikawa, O.; Konishi, H. J. Chem. Soc., Perkin Trans. 1 1999, 1547.
12. (d) Yavari, I.; Esmaili, A. A.; Ramazani, A.; Bolbol-Amiri, A. R. Monatsh. Chem. 1997, 128, 927.
13. (e) Kikugawa, Y.; Kuramoto, M.; Saito, I.; Yamada, S.-I. Chem. Pharm. Bull. 1972, 21, 1914.
14. (f) Johnson, W. S.; Buell, B. G. J. Am. Chem. Soc. 1952, 74, 4517.
15. (g) Kobayashi, K.; Nagato, S.; Kawakita, M.; Morikawa, O.; Konishi, H. Chem. Lett. 1995, 575.
16. (h) Kouznetsov, V.; Palma, A.; Ewert, C.; Varlamov, A. J. Heterocycl. Chem. 1998, 35, 761.
17. (i) Schweizer, E. E.; Smucker, L. D. J. Org. Chem. 1966, 31, 3146.
18. (j) Arisawa, M.; Theeraladanon, C.; Nishida, A.; Nakagawa, M. Tetrahedron Lett. 2001, 42, 8029.
19. (a) Grignon-Dubois, M.; Diaba, F.; Grellier-Marly, M.-C. Synthesis 1994, 800.
20. (b) Diaba, F.; Houerou, C. L.; Grignon-Dubois, M.; Gerval, P. J. Org. Chem. 2000, 65, 907.
21. (c) Diaba, F.; Lewis, I.; Grignon-Dubois, M.; Navarre, S. J. Org. Chem. 1996, 61, 4830.
22. (d) Grignon-Dubois, M.; Diaba, F. J. Chem. Res., Synop. 1998, 660.
23. (e) Maeda, M. Chem. Pharm. Bull. 1990, 38, 2577.
24. (f) Mani, N. S.; Chen, P.; Jones, T. K. J. Org. Chem. 1999, 64, 6911.
25. (g) Muren, J. F.; Weissman, A. J. Med. Chem. 1971, 14, 49.
26. (a) Kim, J. N.; Lee, H. J.; Lee, K. Y.; Kim, H. S. Tetrahedron Lett. 2001, 42, 3737.
27. (b) Kim, J. N.; Kim, H. S.; Gong, J. H.; Chung, Y. M. Tetrahedron Lett. 2001, 42, 8341.
28. Makino, K.; Kara, O.; Takiguchi, Y.; Katano, T.; Asakawa, Y.; Hatano, K.; Hamada, Y. Tetrahedron Lett. 2003, 44, 8925.
29. For reviews of the Morita-Baylis-Hillman reaction, see: (a) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653.
30. (b) Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001.
31. (c) Ciganek, E. In Organic Reactions, Vol. 51; Paquette, L. A., Ed.; Wiley: New York, 1997, 201.
32. (d) Langer, P. Angew. Chem. Int. Ed. 2000, 39, 3049.
33. (e) Kim, J. N.; Lee, K. Y. Curr. Org. Chem. 2002, 6, 627.
34. (f) Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811.
35. (a) Kaye, P. T.; Nocanda, X. W. J. Chem. Soc., Perkin Trans. 1 2000, 1331.
36. (b) Kaye, P. T.; Nocanda, X. W. J. Chem. Soc., Perkin Trans. 1 2002, 1318.
37. Kaye, P. T.; Nocanda, X. W. Synthesis 2001, 2389.
38. Kaye, P. T.; Musa, M. A.; Nocanda, X. W. Synthesis 2003, 531.
39. (a) Familoni, O. B.; Kaye, P. T.; Klass, P. J. Chem. Commun. 1998, 2563.
40. (b) Kim, J. N.; Lee, K. Y.; Kim, H. S.; Kim, T. Y. Org. Lett. 2000, 2, 343.
41. Hong, W. P.; Lee, K.-J. Synthesis 2005, 33; and references cited therein.
42. Basavaiah, D.; Pandiaraju, S. Tetrahedron 1996, 52, 2261.
43. (a) Michaelis, A.; Kaehne, R. Chem. Ber. 1898, 31, 1048.
44. (b) Arbuzov, A. E. J. Russ. Phys. Chem. Soc. 1906, 38, 687.
45. (c) Bhattacharya, A. K.; Thyagarajan, G. Chem. Rev. 1981, 81, 415.
46. (a) Song, Y. S.; Lee, C. H.; Lee, K.-J. J. Heterocycl. Chem. 2003, 40, 939.
47. (b) Lee, C. H.; Song, Y. S.; Cho, H. I.; Yang, J. W.; Lee, K.-J. J. Heterocycl. Chem. 2003, 40, 1103.
48. (c) Ko, S. H.; Lee, K.-J. J. Heterocycl. Chem. 2004, 41, 613.
49. (d) Lee, C. H.; Lee, K.-J. Synthesis 2004, 1941.
50. Staudinger, H.; Meyer, J. Helv. Chim. Acta 1919, 2, 635.
51. (a) For the known compound 9d, see: Basavaiah, D.; Reddy, R. M.; Kumaragurubaran, N.; Sharada, D. Tetrahedron 2002, 58, 3693.
52. (b) The efforts on the isolation of compounds 7d-f were unsuccessful.
53. Suginome, M.; Fukuda, T.; Ito, Y. Org. Lett. 1999, 1, 1977.
54. Fusco, R.; Bianchetti, G.; Pocar, D.; Ugo, R. Gazz. Chim. Ital. 1962, 92, 1040;
55. Chem. Abstr. 1963, 58, 73330.
56. Iyobe, A.; Uchida, M.; Kamata, K.; Hotei, Y.; Kusama, H.; Harada, H. Chem. Pharm. Bull. 2001, 49, 822.
57. Shi, M.; Li, C-Q.; Jiang, J.-K. Tetrahedron 2003, 59, 1181.