Synthesis and aminolysis of N-(4-chlorophenyl)- and N-(2,4-dichlorophenylsulfonyl)-N-(glycidyl)bicyclo-[2.2.1]hept-5-en-endo-ylmethylamines

Author： Kas’yan L. Prid’ma S. Pal’chikov V. Kas’yan A. Turov A. Tokar’ A. Tret’yakov S.

Publisher： MAIK Nauka/Interperiodica

ISSN： 1070-4280

Source： Russian Journal of Organic Chemistry, Vol.46, Iss.5, 2010-05, pp. : 637-643

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Abstract

A glycidyl fragment was introduced into molecules of derivatives of bicyclo[2.2.1]hept-5-en-endo-2-ylmethylamine (sulfonamides, sulfonylurea) under the conditions of phase-transfer catalysis; carboxamides were established to be passive in this reaction; the results were compared with the calculations of the proton affinity of the nitrogen atoms in the molecules of the acyl derivatives of the framework amine. Products were obtained from reactions of N-(4-chlorophenylsulfonyl)-N-(glycidyl)bicyclo[2.2.1]hept-5-en-endo-2-ylmethylamine with benzylamine, N-benzylpiperazine, and bicyclic framework amines. The regiochemistry of the aminolysis was investiganted with the help of NMR ¹H, ¹³C spectra, and also with the use of 2D spectra COSY, NOESY, HMQC, HMBC.