Heteroaromatic N-Imines

Advances in Heterocyclic Chemistry

Volumn 17, Issue C, 1974, Pages 213-253

  Timpe, Hans Joachim ^a  

^a Technical University for Chemistry   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001071927     PISSN: 00652725     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S0065-2725(08)60909-5     Document Type: Article

References (172)

1. Ochiai, E., “Aromatic N-Oxides.”, 1967, Elsevier, Amsterdam.
2. Katritzky, A.R., Lagowski, J.M., “Heteroaromatic N-Oxides.”, 1970, Academic Press, New York.
3. Johnson, A.W., “Ylid Chemistry.”, 1966, Academic Press, New York.
4. Musker, W.K., Fortschr. Chem. Forsch., 14, 1970, 295.
5. Love, P.A., Chem. Ind. (London), 1970, 1070.
6. Timpe, H.-J., Z. Chem., 12, 1972, 250.
7. Sisler, H.H., Omietanski, G.M., Rudner, B., Chem. Rev., 57, 1957, 1021.
8. Gösl, R., Meuwsen, A., Chem. Ber., 92, 1959, 2521.
9. Angew. Chem., 69, 1957, 754.
10. Gösl, R., Meuwsen, A., Org. Syn., 43, 1963, 1.
11. Palmer, M.H., McIntyre, P.S., Tetrahedron Lett., 1968, 2147.
12. Okamoto, T., Hirobe, M., Tamai, Y., Yabe, E., Chem. Pharm. Bull., 14, 1966, 506.
13. Okamoto, T., Hirobe, M., Ohsawa, A., J. Pharm. Bull. Jap., 14, 1966, 518.
14. Okamoto, T., Hirobe, M., Mizushima, C., Ohsawa, A., J. Pharm. Soc. Jap. (Yakugaku Zasshi), 83, 1963, 308.
15. Okamoto, T., Hirobe, M., Yabe, E., Chem. Pharm. Bull., 14, 1966, 523.
16. Potts, K.T., Burton, H.R., Bhattacharyya, J., J. Org. Chem., 31, 1966, 260.
17. Downes, J.E., J. Chem. Soc. C, 1967, 2192.
18. Cullum, V., Farmer, J.B., Hardley, B.L., J. Pharmacol. Chemother., 31, 1967, 435.
19. Epsztajn, J., Lunt, E., Katritzky, A.R., Tetrahedron, 26, 1970, 1665.
20. Sasaki, T., Kanematsu, K., Kakehi, A., Ichikawa, I., Hayakawa, K., J. Org. Chem., 35, 1970, 426.
21. Balasubramanian, McIntosh, J.M., Snieckus, V., J. Org. Chem., 35, 1970, 433.
22. Hoegerle, K., Helv. Chim. Acta, 41, 1958, 539.
23. Rees, C.W., Yelland, M., J. Chem. Soc. Perkin Trans., I, 1972, 77.
24. Moore, J.A., Binkert, J., J. Amer. Chem. Soc., 81, 1959, 6045.
25. Tamura, Y., Tsujimoto, N., Ikeda, M., J. Chem. Soc. D, 1971, 310.
26. Tamura, Y., Tsujimoto, N., Sumida, Y., Ikeda, M., Tetrahedron, 28, 1972, 21.
27. Zincke, T., Heuser, G., Möller, W., Ann., 333, 1904, 296.
28. Vompe, A.F., Turitsyana, N.F., Zh. Obshch. Khim., 27, 1957, 3282.
29. Chem. Abstr., 52, 1958, 9112.
30. Dufton, S.F., J. Chem. Soc., 61, 1892, 785.
31. Perkin, W.H., Robinson, R., J. Chem. Soc., 103, 1913, 1978.
32. Beyer, H., Leverenz, K., Schilling, H., Angew. Chem., 73, 1961, 272.
33. Beyer, H., Thieme, E., J. Prakt. Chem., 31(4), 1966, 293.
34. Tamura, Y., Tsujimoto, N., Chem. Ind. (London), 1970, 926.
35. Tamura, Y., Tsujimoto, N., Mano, M., Chem. Pharm. Bull., 19, 1971, 130.
36. Schneider, W., Seebach, F., Chem. Ber., 54, 1921, 2285.
37. Schneider, W., Ann., 438, 1924, 115.
38. Schneider, W., Müller, W., Ann., 438, 1924, 147.
39. Schneider, W., Riedel, W., Chem. Ber., 74, 1941, 1252.
40. Schneider, W., Weiss, K., Chem. Ber., 61, 1928, 2445.
41. Dimroth, K., Arnoldy, G., von Eicken, S., Schiffer, G., Ann., 604, 1957, 221.
42. Balaban, A.T., Frangopol, P.T., Mateescu, G., Nenitzescu, C.D., Bull. Soc. Chim. Fr., 1962, 298.
43. Balaban, A.T., Tetrahedron, 24, 1968, 5059.
44. Pedersen, C.L., Harrit, N., Buchardt, O., Acta Chem. Scand., 24, 1970, 3435.
45. Lempert, K., Acta Chim. Sci. Hung., 65, 1970, 443.
46. El-Kholy, I.El-S., Rafla, F.K., Soliman, G., J. Chem. Soc., 1961, 4490.
47. El-Kholy, I.S., Rafla, F.K., J. Chem. Soc. C, 1969, 974.
48. Moore, J.A., J. Amer. Chem. Soc., 77, 1955, 3417.
49. Moore, J.A., Binkert, J., J. Amer. Chem. Soc., 81, 1959, 6029.
50. Moore, J.A., Trans. N. Y. Acad. Sci., 27, 1965, 591.
51. Moore, J.A., Pleiss, G., J. Amer. Chem. Soc., 90, 1968, 4738.
52. Moore, J.A., Marascia, F.J., Medeiros, R.W., Wineholt, R.L., J. Org. Chem., 31, 1966, 34.
53. Moore, J.A., Volker, E.V., Kopay, C.M., J. Org. Chem., 36, 1971, 2676.
54. Lwowski, W., “Nitrenes.”, 1970, Wiley (Intersciences), New York.
55. Hünig, S., Helv. Chim. Acta, 54, 1971, 1721.
56. Curtius, T., Rissom, J., J. Prakt. Chem., 125(2), 1930, 311.
57. Curtius, T., Kraemer, G., J. Prakt. Chem., 125(2), 1930, 323.
58. Curtius, T., Vorbach, K., J. Prakt. Chem., 125(2), 1930, 340.
59. Curtius, T., Bottler, H., J. Prakt. Chem., 125(2), 1930, 380.
60. Ashley, J.N., Buchanan, G.L., Easson, A.P.T., J. Chem. Soc., 1947, 60.
61. Buchanan, G.L., Levine, R.M., J. Chem. Soc., 1950, 2248.
62. Hafner, K., Zinser, D., Moritz, K.-L., Tetrahedron Lett., 1964, 1733.
63. Datta, P.K., J. Indian Chem. Soc., 24, 1947, 109.
64. Abramovitch, R.A., Davis, B.A., Chem. Rev., 64, 1964, 149.
65. Prosser, T.J., Marcantonio, A.F., Breslow, D.S., Tetrahedron Lett., 1964, 2779.
66. Marsh, F.D., U. S. Patent 3,624,256 1971.
67. 50 Lwowski, p. 279.
68. Abramovitch, R.A., Takaya, T., J. Org. Chem., 37, 1972, 2022.
69. Streith, J., Cassal, J.-M., Bull. Soc. Chim. Fr., 1969, 2175.
70. Kan, G., Thomas, M.T., Snieckus, V., J. Chem. Soc. D., 1971, 1022.
71. Streith, J., Luttringer, J.P., Nastasi, M., J. Org. Chem., 36, 1971, 2962.
72. Hoffmann, R., Woodward, R.B., Accounts Chem. Res., 1, 1968, 17.
73. Epsztajn, J., Katritzky, A.R., Tetrahedron Lett., 1969, 4739.
74. Okamoto, T., Horikiri, H., Hayashi, S., Hirobe, M., Yakugaku Zasshi, 91, 1971, 210.
75. Chem. Abstr., 74, 1971, 99818k.
76. Okamoto, T., Horikiri, H., Hayashi, S., Hirobe, M., Yakugaku Zasshi, 91, 1971, 216.
77. Chem. Abstr., 74, 1971, 99819m.
78. Okamoto, T., Hirobe, M., Yamazaki, T., Chem. Pharm. Bull., 14, 1966, 512.
79. Tamura, Y., Ishibashi, H., Tsujimoto, N., Ikeda, M., Chem. Pharm. Bull., 19, 1971, 1285.
80. Shiba, T., Yamane, K., Kato, H., J. Chem. Soc. D, 1970, 1592.
81. Huisgen, R., Grashey, R., Krischke, R., Tetrahedron Lett., 1962, 387.
82. Tamura, Y., Tsujimoto, N., Uchimura, M., Chem. Pharm. Bull., 19, 1971, 143.
83. Zincke, T., Weisspfenning, G., Ann., 396, 1913, 103.
84. Gait, S.F., Rees, C.W., Storr, R.C., J. Chem. Soc. D., 1971, 1545.
85. Becker, H.G.O., Böttcher, H., Röthling, T., Timpe, H.-J., Wiss. Z. Tech. Hochschule Chem. “Carl Schorlemmer” Leuna-Merseburg, 8, 1966, 22.
86. Becker, H.G.O., Sauder, N., Timpe, H.-J., J. Prakt. Chem., 311, 1969, 897.
87. Becker, H.G.O., Timpe, H.-J., J. Prakt. Chem., 312, 1970, 1112.
88. Becker, H.G.O., Heimburger, K., Timpe, H.-J., J. Prakt. Chem., 313, 1971, 795.
89. Boyd, G.V., Dando, S.R., J. Chem. Soc. C, 1970, 1397.
90. Boyd, G.V., Summers, A.J.H., J. Chem. Soc. C, 1971, 409.
91. Runti, C., Nisi, C., J. Med. Chem., 7, 1964, 814.
92. Boyd, G.V., Summers, A.J.H., J. Chem. Soc. B, 1971, 1648.
93. Timpe, H.-J., unpublished results, see Promotion-B-Thesis, TH Chemie, Merseburg, 1972.
94. Shvaika, O.P., Fomenko, W.I., Dokl. Akad. Nauk SSSR, 200, 1971, 134.
95. Huisgen, R., Anselme, J.P., Chem. Ber., 98, 1965, 2998.
96. Timpe, H.-J., Z. Chem., 11, 1971, 340.
97. Carboni, R.A., Castle, J.E., J. Amer. Chem. Soc., 84, 1962, 2453.
98. Pfleger, R., Garthe, E., Rauer, K., Chem. Ber., 96, 1963, 1827.
99. Bauer, H., Bedford, G.R., Katritzky, A.R., J. Chem. Soc., 1964, 751.
100. Chinone, A., Huseya, Y., Ohta, M., Bull. Chem. Soc. Jap., 43, 1970, 2650.
101. Huseya, Y., Chinone, A., Ohta, M., Bull. Chem. Soc. Jap., 44, 1971, 1667.
102. Märky, M., Hansen, H.-J., Schmid, H., Helv. Chim. Acta, 54, 1971, 1275.
103. Angadiyavar, C.S., George, M.V., J. Org. Chem., 36, 1971, 1589.
104. Fraser, R.R., Gurudatta, M.M., Haque, K.E., J. Org. Chem., 34, 1969, 4118.
105. Scheiner, R., Dinda, J.F., Tetrahedron, 26, 1970, 2619.
106. Scheiner, P., J. Org. Chem., 34, 1960, 199.
107. Clovis, J.S., Eckell, A., Huisgen, R., Sustmann, R., Chem. Ber., 100, 1967, 60.
108. Spasov, A.V., Elenko, D., Robev, S., Bulg. Akad. Nauk, Otd. Geol.-Geogr. Khim. Nauk, Izv. Khim. Inst., 1, 1951, 217.
109. Chem. Abstr., 47, 1953, 2153 2, 3(1953).
110. Chem. Abstr., 49, 1955, 5372.
111. Woodward, R.B., Wintner, C., Tetrahedron Lett., 1969, 2697.
112. Buckingham, J., Quart. Rev. (London), 23, 1969, 37.
113. Wintner, C., Tetrahedron Lett., 1970, 2275.
114. Angadiyavar, G.S., Sukumaran, K.B., George, M.V., Tetrahedron Lett., 1971, 633.
115. Pechmann, H., Bauer, W., Chem. Ber., 33, 1900, 645.
116. Pechmann, H., Bauer, W., Chem. Ber., 42, 1909, 664.
117. Stollé, R., Chem. Ber., 59, 1926, 1742.
118. Petersen, S., Heitzer, H., Angew. Chem., 82, 1970, 81.
119. 114.
120. Alexandrou, N.E., Micromastoras, E.D., Tetrahedron Lett., 1968, 231.
121. Curtin, D.Y., Alexandrou, N.E., Tetrahedron, 19, 1967, 1697.
122. Alexandrou, N.E., Tetrahedron, 22, 1966, 1309.
123. Bauer, H., Boulton, A.J., Fedeli, W., Katritzky, A.R., Majid-Hamid, A., Mazza, F., Vaciago, A., Angew. Chem., 83, 1971, 115.
124. Staab, H.A., Angew. Chem., 74, 1962, 407.
125. Angew. Chem. Int. Ed. Engl., 1, 1962, 351.
126. Szymanski, H.A., “Theory and Practice of Infrared Spectroscopy.”, 1964, Plenum, New York.
127. Brügel, W., “Einführung in die Ultrarotspektroskopie.”, 1962, Steinkopff, Darmstadt.
128. Brownlee, R.T., Hutchinson, R.E.J., Katritzky, A.R., Tidwell, T.T., Topsom, R.D., J. Amer. Chem. Soc., 90, 1968, 1757.
129. Katritzky, A.R., Palmer, C.R., Swinbourne, F.J., Tidwell, T.T., Topsom, R.D., J. Amer. Chem. Soc., 91, 1969, 636.
130. Timpe, H.-J., Wiss. Z. Tech. Hochschule Chem. “Carl Schorlemmer” Leuna-Merseburg, 14, 1972, 102.
131. Gleiter, R., Schmidt, D., Streith, J., Helv. Chim. Acta, 54, 1971, 1645.
132. Reichardt, Ch., Dimroth, K., Fortschr. Chem. Forsch., 11, 1968, 1.
133. Becker, H.G.O., Timpe, H.-J., Chimia, 26, 1972, 473.
134. Fowler, F.W., Katritzky, A.R., Rutherford, R.J.D., J. Chem. Soc. B, 1971, 460.
135. Ikeda, M., Tsujimoto, N., Tamura, Y., Org. Mass Spectrom., 5, 1971, 935.
136. Lightner, D.A., Nicoletti, R., Qiustad, G.B., Irwin, E., Org. Mass Spectrom., 4, 1970, 571 and the references cited therein.
137. Ikeda, M., Tsujimoto, N., Tamura, Y., Org. Mass Spectrom., 5, 1971, 61.
138. Becker, H.G.O., Beyer, D., Timpe, H.-J., Z. Chem., 10, 1970, 264.
139. Ikeda, M., Tsujimoto, N., Tamura, Y., Org. Mass Spectrom., 5, 1971, 389.
140. Ikeda, M., Kato, S., Sumida, Y., Tamura, Y., Org. Mass Spectrom., 5, 1971, 1383.
141. Bentley, T.W., Johnstone, R.A., Advan. Phys. Organ. Chem., 8, 1970, 152.
142. Timpe, H.-J., Becker, H.G.O., J. Prakt. Chem., 314, 1972, 325.
143. Becker, H.G.O., Nagel, D., Timpe, H.-J., J. Prakt. Chem., 315, 1973, 97.
144. Wanzlick, H.W., Angew. Chem., 74, 1962, 122.
145. Quast, H., Hünig, S., Chem. Ber., 99, 1966, 2017.
146. Becker, H.G.O., Timpe, H.-J., J. Prakt. Chem., 311, 1969, 9.
147. Snieckus, V., Kan, G., Tetrahedron Lett., 1970, 2267.
148. Huisgen, R., Angew. Chem., 75, 1963, 621.
149. Okamoto, T., Hirobe, M., Tamai, Y., Chem. Pharm. Bull., 11, 1963, 1089.
150. Okamoto, T., Hirobe, M., Mizushima, C., Ohsawa, A., Chem. Pharm. Bull., 11, 1963, 781.
151. Boekelheide, V., Fedoruk, N.A., J. Org. Chem., 33, 1968, 2062.
152. Sasaki, T., Kanematsu, K., Yukimoto, Y., J. Chem. Soc. C, 1970, 481.
153. Tamura, Y., Yamakami, A., Ikeda, M., J. Pharm. Soc. Jap. (Yakugaku Zasshi), 91, 1971, 1154.
154. Sasaki, T., Kanematsu, K., Kakehi, A., J. Org. Chem., 36, 1971, 2451.
155. Sasaki, T., Kanenatsu, K., Kakehi, A., J. Org. Chem., 36, 1971, 2978.
156. H.-J. Timpe, unpublished observation.
157. Timpe, H.-J., Z. Chem., 12, 1972, 333.
158. Kurbatov, Y.V., Zalyalieva, S.V., Oschtroshenko, O.S., Sadykov, A.S., Arb. Samarkand. Gos. Univ., 167, 1969, 185.
159. Chem. Abstr., 75, 1971, 48837d.
160. Lund, H., Advan. Heterocycl. Chem., 12, 1970, 311.
161. Michalska, M., Tetrahedron Lett., 1971, 2267.
162. Streith, J., Cassal, J.-M., Angew. Chem., 80, 1968, 117.
163. Angew. Chem. Int. Ed. Engl., 7, 1968, 129.
164. Streith, J., Cassal, J.-M., Tetrahedron Lett., 1968, 5441.
165. Streith, J., Sigwalt, C., Bull. Soc. Chim. Fr., 1970, 1157.
166. Sasaki, S., Kanematsu, K., Kakehi, A., J. Chem. Soc. D, 1969, 432.
167. Snieckus, V., J. Chem. Soc. D, 1969, 831.
168. Spence, G.G., Taylor, E.C., Buchardt, O., Chem. Rev., 70, 1970, 231.
169. Schulz, M., West, G., J. Prakt. Chem., 312, 1970, 161.
170. Snieckus, V., Kan, G., J. Chem. Soc. D., 1970, 172.
171. Potts, K.T., Dugas, R., J. Chem. Soc. D., 1970, 732.
172. Bird, C.W., Wong, D.Y., Boyd, G.V., Summers, A.J.H., Tetrahedron Lett., 1971, 3187.