Aza-Annulation of Enamine Related Substrates with a,b-Unsaturated Carboxylate Derivatives as a Route to the Selective Synthesis of d-Lactams and Pyridones

Studies in Natural Products Chemistry

Volumn 18, Issue PK, 1995, Pages 315-389

  Stille, John R ^a   Barta, Nancy S ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000848741     PISSN: 15725995     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S1572-5995(96)80030-5     Document Type: Chapter

References (143)

1. (1)(a) Ninomiya, I., Naito, T., Heterocycles, 15, 1981, 1433.
2. (1)(b) Ninomiya, I., Miyata, O., Atta-ur-Rahman, (eds.) Studies in Natural Products Chemistry, Vol. 3, 1989, Elsevier, New York, 399.
3. (1)(c) Ninomiya, I., Naito, T., Brossi, A., (eds.) The Alkaloids, Vol. 22, 1983, Academic Press, New York, 189.
4. (2) Vill, J.J., Steadman, T.R., Godfrey, J.J., J. Org. Chem., 29, 1964, 2780.
5. (3) Kuehne, M.E., Bornmann, W.G., Parsons, W.H., Spitzer, T.D., Blount, J.F., Zubieta, J., J. Org. Chem., 53, 1988, 3439.
6. (4) Chelucci, G., Cossu, S., Scano, G., Soccolini, F., Heterocycles, 31, 1990, 1397.
7. (5) Murahashi, S.-I., Sasao, S., Saito, E., Naota, T., J. Org. Chem., 57, 1992, 2521.
8. (6) Tominaga, Y., Kawabe, M., Hosomi, A., J. Heterocycl. Chem., 24, 1987, 1325.
9. (7) Stork, G., Pure and Appl. Chem., 17, 1968, 383.
10. (8) Ninomiya, I., Naito, T., Higuchi, S., Mori, T., J. Chem. Soc., Chem. Commun., 1971, 457.
11. (9) El-Barbary, A.A., Carlsson, S., Lawesson, S.-O., Tetrahedron, 38, 1982, 405.
12. (10) Hickmott, P.W., Rae, B., Pienaar, D.H., S. Afr. J. Chem., 41, 1988, 85.
13. (11)(a) Xia, Y., Kozikowski, A.P., J. Am. Chem. Soc., 111, 1989, 4116.
14. (11)(b) Kozikowski, A.P., Xia, Y., Reddy, E.R., Tückmantel, W., Hanin, I., Tang, X.C., J. Org. Chem., 56, 1991, 4636.
15. (12) Stork, G., Kretchmer, R.A., Schlessinger, R.H., J. Am. Chem. Soc., 90, 1968, 1647.
16. (13) Paronikyan, E.G., Sirakanyan, S.N., Lindeman, S.V., Aleksanyan, M.S., Karapetyan, A.A., Noravyan, A.S., Struchkov, Y.T., Chem. Heterocycl. Compd. (USSR) (Engl. Transl.), 25, 1990, 953.
17. (13) Paronikyan, E.G., Sirakanyan, S.N., Lindeman, S.V., Aleksanyan, M.S., Karapetyan, A.A., Noravyan, A.S., Struchkov, Y.T., Khim. Geterotsikl. Soedin., 1989, 1137.
18. (14)(a) Sammour, A., Alkady, M., Ind. J. Chem., 12, 1974, 51.
19. (14)(b) El-Kady, M., El-Hashash, M.A., Sayed, M.A., El-Sherif, M., Ind. J. Chem., Sect. B, 20, 1981, 491.
20. (15) Briet, P.; Berthelon, J.-J.; Depin, J.-C. European Patent 0 000 306, 1979.
21. (15) Briet, P., Berthelon, J.-J., Depin, J.-C., Chem. Abstr., 91, 1979, 20479v.
22. (16) Elgemeie, G.E.H., Elghandour, A.H.H., Bull. Chem. Soc. Jpn., 63, 1990, 1230.
23. (17) Kambe, S., Saito, K., Sakurai, A., Hayashi, T., Synthesis, 1977, 841.
24. (18) Takahashi, K., Miyake, A., Hata, G., Bull. Chem. Soc. Jpn., 45, 1972, 2212.
25. (19) Norman, M.H., Heathcock, C.H., J. Org. Chem., 53, 1988, 3370.
26. (20) Gardette, D., Gramain, J.-C., Sinibaldi, M.-E., Heterocycles, 31, 1990, 1439.
27. (21) Borne, R.F., Fifer, E.K., Waters, I.W., J. Med. Chem., 27, 1984, 1271.
28. (22) Wenkert, E., Chauncy, B., Dave, K.G., Jeffcoat, A.R., Schell, F.M., Schenk, H.P., J. Am. Chem. Soc., 95, 1973, 8427.
29. (23) Ito, K., Yokokura, S., Miyajima, S., J. Heterocycl. Chem., 26, 1989, 773.
30. (24) Kmetic, M., Stanovnik, B., Tisler, M., Kappe, T., Heterocycles, 35, 1993, 1331.
31. (25)(a) Meyers, A.I., Reine, A.H., Sircar, J.C., Rao, K.B., Singh, S., Weidmann, H., Fitzpatrick, M., J. Heterocycl. Chem., 5, 1968, 151.
32. (25)(b) Horii, Z.-i., Iwata, C., Ninomiya, I., Imamura, N., Ito, M., Tamura, Y., Chem. Pharm. Bull., 12, 1964, 1405.
33. (26) Shabana, R., Rasmussen, J.B., Olesen, S.O., Lawesson, S.-O., Tetrahedron, 36, 1980, 3047.
34. (27) Kozikowski, A.P., Reddy, E.R., Miller, C.P., J. Chem. Soc., Perkin Trans. 1, 1990, 195.
35. (28) Paulvannan, K., Stille, J.R., J. Org. Chem., 57, 1992, 5319.
36. (29) Ninomiya, I., Naito, T., Higuchi, S., J. Chem. Soc., Chem. Commun., 1970, 1662.
37. (30) Hickmott, P.W., Sheppard, G., J. Chem. Soc. (C), 1971, 1358.
38. (31)(a) Rigby, J.H., Balasubramanian, N., J. Org. Chem., 49, 1984, 4569.
39. (31)(b) Rigby, J.H., Qabar, M., Synth. Commun., 20, 1990, 2699.
40. (32)(a) Dickman, D.A., Heathcock, C.H., J. Am. Chem. Soc., 111, 1989, 1528.
41. (32)(b) Heathcock, C.H., Norman, M.H., Dickman, D.A., J. Org. Chem., 55, 1990, 798.
42. (33)(a) Aranda, V.G., Barluenga, J., Gotor, V., Tetrahedron Lett., 1973, 2819.
43. (33)(b) Barluenga, J., Muñiz, L., Palacios, F., Goto, V., J. Heterocycl. Chem., 20, 1983, 65.
44. (34) Aranda, V.G., Barluenga, J., Gotor, V., Tetrahedron Lett., 1974, 977.
45. (35) Janin, Y.L., Bisagni, E., Carrez, D., J. Heterocycl. Chem., 30, 1993, 1129.
46. (36) Kametani, T., Terasawa, H., Ihara, M., J. Chem. Soc., Perkin Trans. 1, 1976, 2547.
47. (37) Kametani, T., Terasawa, H., Ihara, M., Fukumoto, K., Heterocycles, 6, 1977, 37.
48. (38) Ihara, M., Noguchi, K., Ohsawa, T., Fukumoto, K., Kametani, T., Heterocycles, 19, 1982, 1829.
49. (39) Kametani, T., Suzuki, Y., Terasawa, H., Ihara, M., J. Chem. Soc., Perkin Trans. I, 1979, 1211.
50. (40) Kametani, T., Suzuki, Y., Ihara, M., Can. J. Chem., 57, 1979, 1679.
51. (41) Bhattacharjya, A., Bhattacharya, P.K., Pakrashi, S.C., Heterocycles, 20, 1983, 2397.
52. (42)(a) Danieli, B., Lesma, G., Palmisano, G., J. Chem. Soc., Chem. Commun., 1980, 109.
53. (42)(b) Danieli, B., Lesma, G., Palmisano, G., Gazz. Chim. Ital., 111, 1981, 257.
54. (43) Danieli, B., Lesma, G., Palmisano, G., Tollari, S., Synthesis, 1984, 353.
55. (44)(a) Kametani, T., Kanaya, N., Ihara, M., Heterocycles, 16, 1981, 925.
56. (44)(b) Kametani, T., Kanaya, N., Hino, H., Huang, S.-P., Ihara, M., J. Chem. Soc., Perkin Trans. I, 1981, 3168.
57. (45) Kametani, T., Kanaya, N., Hino, H., Huang, S.-P., Ihara, M., Heterocycles, 14, 1980, 1771.
58. (46) Calabi, L., Danieli, B., Lesma, G., Palmisano, G., Tetrahedron Lett., 23, 1982, 2139.
59. (47) Kametani, T., Ohsawa, T., Ihara, M., J. Chem. Soc., Perkin Trans. I, 1981, 1563.
60. (48) Corriu, R.J.P., Perz, R., Tetrahedron Lett., 26, 1985, 1311.
61. (49) Singh, B., Synthesis, 1985, 305.
62. (50) Singh, B. U.S. Patent 4 347 363, 1982.
63. (50) Singh, B., Chem. Abstr., 97, 1982, 216018n.
64. (51) Tanabe Seiyaku KK Japanese Patent J4-8 023 779, 1984.
65. (52) Horii, Z.-I., Iwata, C., Tamura, Y., Nelson, N.A., Rasmusson, G.H., J. Org. Chem., 29, 1964, 2768.
66. (53)(a) Cannon, J.G., Hatheway, G.J., Long, J.P., Sharabi, F.M., J. Med. Chem., 19, 1976, 987.
67. (53)(b) Cannon, J.G., Suarez-Gutierrez, C., Lee, T., Long, J.P., Costall, B., Fortune, D.H., Naylor, R.J., J. Med. Chem., 22, 1979, 341.
68. (53)(c) Cannon, J.G., Hamer, R.L., Ilhan, M., Bhatnagar, R.K., Long, J.P., J. Med. Chem., 27, 1984, 190.
69. (53)(d) Cannon, J.G., Chang, Y., Amoo, V.E., Walker, K.A., Synthesis, 1986, 494.
70. (54) Jones, C.D., Audia, J.E., Lawhorn, D.E., McQuaid, L.A., Neubauer, B.L., Pike, A.J., Pennington, P.A., Stamm, N.B., Toomey, R.E., Hirsch, K.S., J. Med. Chem., 36, 1993, 421.
71. (55) Ninomiya, I., Kiguchi, T., J. Chem. Soc., Chem. Commun., 1976, 624.
72. (56) Hickmott, P.W., Sheppard, G., J. Chem. Soc. (C), 1971, 2112.
73. (57) Paulvannan, K., Stille, J.R., Tetrahedron Lett., 34, 1993, 8197.
74. (58) Cook, G.R., Beholz, L.G., Stille, J.R., J. Org. Chem., 59, 1994, 3575.
75. (59) Paulvannan, K., Stille, J.R., J. Org. Chem., 59, 1994, 1613.
76. (60) Huizenga, R.H., van Wiltenburg, J., Pandit, U.K., Tetrahedron Lett., 30, 1989, 7105.
77. (61) Augustin, M., Frank, J., Köhler, M., J. Prakt. Chem., 326, 1984, 594.
78. (62) Singh, B., Lesher, G.Y., J. Heterocycl. Chem., 27, 1990, 2085.
79. (63) Lielbriedis, I.E., Kampare, R.B., Dubur, G.Y., Latv. PSR Zinat. Akad. Vestis., Kim. Ser., 2, 1990, 212.
80. (64) Paulvannan, K., Stille, J.R., Tetrahedron Lett., 42, 1993, 6673.
81. (65)(a) Leniewski, A., Szychowski, J., MacLean, D.B., Can. J. Chem., 59, 1981, 2479.
82. (65)(b) Leniewski, A., MacLean, D.B., Saunders, J.K., Can. J. Chem., 59, 1981, 2695.
83. (66) Shono, T., Matsumura, Y., Kashimura, S., J. Org. Chem., 46, 1981, 3719.
84. (67)(a) Wiesner, K., Jirkovsky, I., Fishman, M., Williams, C.A.J., Tetrahedron Lett., 1967, 1523.
85. (67)(b) Wiesner, K., Jirkovsky, I., Tetrahedron Lett., 1967, 2077.
86. (67)(c) Wiesner, K., Poon, L., Jirkovsky, I., Fishman, M., Can. J. Chem., 47, 1969, 433.
87. (68)(a) Sluyter, M.A.T., Pandit, U.K., Speckamp, W.N., Huisman, H.O., Tetrahedron Lett., 1966, 87.
88. (68)(b) Dubas-Sluyter, M.A.T., Speckamp, W.N., Huisman, H.O., Rec. Trav. Chim. Pays-Bas., 91, 1972, 157.
89. (69) Wolf, U., Sucrow, W., Vetter, H.-J., Z. Naturforsch., 34b, 1979, 102.
90. (70) Marcos, A., Pedregal, C., Avendaño, C., Tetrahedron, 50, 1994, 12941.
91. (71) Barluenga, J., Jardón, J., Gotor, V., Synthesis, 1988, 146.
92. (72) Barluenga, J., Iglesias, M.J., Gotor, V., Synthesis, 1987, 662.
93. (73) Schroll, G., Klemmensen, P., Lawesson, S.-O., Ark. Kemi., 26, 1967, 317.
94. (74) Paulvannan, K., Schwarz, J.B., Stille, J.R., Tetrahedron Lett., 34, 1993, 215.
95. (75) Cook, G.R., Beholz, L.G., Stille, J.R., Tetrahedron Lett., 35, 1994, 1669.
96. (76) Knoevenagel, E., Fries, A., Chem. Ber., 31, 1989, 761.
97. (77) Sanna, P., Nuvole, A., Sequi, P.A., Paglietti, G., Heterocycles, 36, 1993, 259.
98. (78) Capuano, L., Boschat, P., Müller, I., Zander, R., Schramm, V., Hädicke, E., Chem. Ber., 116, 1983, 2058.
99. (79) Danishefsky, S., Etheredge, S.J., Volkmann, R., Eggler, J., Quick, J., J. Am. Chem. Soc., 93, 1971, 5575.
100. (80) Volkmann, R., Danishefsky, S., Eggler, J., Solomon, D.M., J. Am. Chem. Soc., 93, 1971, 5576.
101. (81) Heber, D., Arch. Pharm., 320, 1987, 445.
102. (82) Ziegler, E., Hradetzky, F., Belegratis, K., Monatsh. Chemie, 96, 1965, 1347.
103. (83) Dannhardt, G., Meindl, W., Schober, B.D., Kappe, T., Eur. J. Med. Chem., 26, 1991, 599.
104. (84) Ried, W., Bätz, F., Liebis Ann. Chem., 762, 1972, 1.
105. (85) Brunerie, P., Célérier, J.-P., Huché, M., Lhommet, G., Synthesis, 1985, 735.
106. (86) Nagasaka, T., Inoue, H., Hamaguchi, F., Heterocycles, 20, 1983, 1099.
107. (87) Nagasaka, T., Inoue, H., Ichimura, M., Hamaguchi, F., Synthesis, 1982, 848.
108. (88) Danishefsky, S., Etheredge, S.J., J. Org. Chem., 39, 1974, 3430.
109. (89) Shen, W., Coburn, C.A., Bornmann, W.G., Danishefsky, S.J., J. Org. Chem., 58, 1993, 611.
110. (90) Fang, F.G., Danishefsky, S.J., Tetrahedron Lett., 30, 1989, 3621.
111. (91) Kawahara, N., Nakajima, T., Itoh, T., Ogura, H., Synthesis, 1985, 644.
112. (92) Kawahara, N., Nakajima, T., Itoh, T., Ogura, H., Heterocycles, 20, 1983, 1721.
113. (93) Chiba, T., Takahashi, T., Chem. Pharm. Bull., 33, 1985, 2731.
114. (94)(a) Beholz, L.G., Ph.D. Thesis, 1994, Michigan State University.
115. (b) Barta, N. S.; Stille, J. R. Unpublished results.
116. (95) Seidel, M.C., J. Org. Chem., 37, 1972, 600.
117. (96) Sato, M., Yoneda, N., Kaneko, C., Chem. Pharm. Bull., 34, 1986, 621.
118. (97) Singh, B., Lesher, G.Y., Brundage, R.P., Synthesis, 1991, 894.
119. (98) Kappe, C.O., Kappe, T., Monatsh. Chemie, 120, 1989, 1095.
120. (99) Yamada, Y., Hatano, K., Matsui, M., Agr. Biol. Chem., 34, 1970, 1536.
121. (100) Openshaw, H.T., Whittaker, N., J. Chem. Soc., 1961, 4939.
122. (101) Thyagarajan, B.S., Gopalakrishnan, P.V., Tetrahedron, 21, 1965, 3305.
123. (102) Thyagarajan, B.S., Gopalakrishnan, P.V., Tetrahedron, 21, 1965, 945.
124. (103) Boekelheide, V., Lodge, J.P. Jr., J. Am. Chem. Soc., 73, 1951, 3681.
125. (104) Bohlmann, V.F., Ottawa, N., Keller, R., Liebigs Ann. Chem., 587, 1954, 162.
126. (105) Kurashina, Y.; Miyata, H.; Momose, D.-I. European Pat 309 260, 1989.
127. (105) Kurashina, Y., Miyata, H., Momose, D.-I., Chem. Abstr., 111, 1989, 153656.
128. (106) Thyagarajan, B.S., Gopalakrishnan, P.V., Tetrahedron, 20, 1964, 1051.
129. (107) Kolar, P., Tisler, M., J. Heterocycl. Chem., 30, 1993, 1253.
130. (108) Forti, L., Gelmi, M.L., Pocar, D., Varallo, M., Heterocycles, 24, 1986, 1401.
131. (109) Adams, R., Reifschneider, W., J. Am. Chem. Soc., 81, 1959, 2537.
132. (110) Tonetti, I., Primofiore, G., Il Farmaco, 35, 1980, 1052.
133. (111)(a) Sevin, A., Masure, D., Giessner-Prettre, C., Pfau, M., Helv. Chim. Acta, 73, 1990, 552.
134. (111)(b) d'Angelo, J., Desmaële, D., Dumas, F., Guingant, A., Tetrahedron: Asymm., 3, 1992, 459.
135. (111)(c) Pfau, M., Tomas, A., Lim, S., Revial, G., J. Org. Chem., 60, 1995, 1143.
136. (112) d'Angelo, J., Guingant, A., Riche, C., Chiaroni, A., Tetrahedron Lett., 29, 1988, 2667.
137. (113) Audia, J.E., Lawhorn, D.E., Deeter, J.B., Tetrahedron Lett., 34, 1993, 7001.
138. (114) Enders, D., Demir, A.S., Puff, H., Franken, S., Tetrahedron Lett., 28, 1987, 3795.
139. Barta, N.S., Brode, A., Stille, J.R., J. Am. Chem. Soc., 116, 1994, 6201.
140. Benovsky, P.; Stille, J. R. Unpublished results.
141. Hua, D.H., Bharathi, S.N., Takusagawa, F., Tsujimoto, A., Panangadan, J.A.K., Hung, M.-H., Bravo, A.A., Erpelding, A.M., J. Org. Chem., 54, 1989, 5659.
142. Hua, D.H., Bharathi, S.N., Panangadan, J.A.K., Tsujimoto, A., J. Org. Chem., 56, 1991, 6998.
143. Hua, D.H., Park, J.-G., Katsuhira, T., Bharathi, S.N., J. Org. Chem., 58, 1993, 2144.