Synthesis and aminolysis of N-(4-chlorophenyl)- and N-(2,4-dichlorophenylsulfonyl)-N-(glycidyl)bicyclo-[2.2.1]hept-5-en-endo-ylmethylamines |
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Authors: | L I Kas’yan S A Prid’ma V A Pal’chikov A O Kas’yan A V Turov A V Tokar’ and S V Tret’yakov |
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Institution: | (1) M. V. Lomonosov Moscow State University, Moscow, 199992, Russia; |
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Abstract: | A glycidyl fragment was introduced into molecules of derivatives of bicyclo2.2.1]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)bicyclo2.2.1]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. |
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