Reactions of 3-[N-chloroacetylamino-N-(4-nitrophenyl)]-2-formylindole with alkylamines |
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Authors: | S. Yu. Ryabova A. S. Shashkov L. M. Alekseeva E. A. Lisitsa V. G. Granik |
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Affiliation: | (1) State Scientific Center for Antibiotics, 3a ul. Nagatinskaya, 117003 Moscow, Russian Federation;(2) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation |
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Abstract: | The reactions of 3-[N-chloracetylamino-N-(4-nitrophenyl)]-2-formylindole (1a) with 2-(N, N-dialkylamino)ethylamines afford complex condensation products 7b,c consisting of two similar but not identical diazepinoindole fragments. For the reaction of compound 1a with 3-(N,N-diethylamino)propylamine, the process occurs in a different manner, and the predominant product is 4-ethylaminopropyl-1-(4-nitrophenyl)-2-oxo-1,2,3,4,5,6-hexahydro[1,4]diazepino[6,5-b]indole hydrocloride (14). Two routes of these unexpected transformations were proposed. The structures of the synthesized products were proved by the 1sH and 13C NMR, HMBC, and HSQC (direct proton-carbon correlation) spectra. Dedicated to Academician V. A. Tartakovsky on the occasion of his 75th birthday. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1536–1542, August, 2007. |
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Keywords: | 3-[N-chloroacetylamino-N-(4-nitrophehyl)]-2-formylindole ethanolamine benzylamine 2-(diethylamino)ethylamine 2-(dimethylamino)ethylamine 3-(diethylamino)propylamine condensation cyclization 1,2,3,6-tetrahydro[1,4]diazepino[6,5-b]indoles 1,2,3,4,5,6-hexahydro[1,4]diazepino[6,5-b]indoles |
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