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1,3‐Dipolar cycloaddition reactions of 3‐acylimino‐1‐methylbenzimidazolium betaines
Author(s) -
Tamura Yasumitsu,
Hayashi Hironori,
Ikeda Masazumi
Publication year - 1975
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570120501
Subject(s) - chemistry , methyl acrylate , acrylonitrile , cycloaddition , 1,3 dipolar cycloaddition , adduct , ethyl acrylate , cleavage (geology) , acrylate , polymer chemistry , medicinal chemistry , photochemistry , organic chemistry , polymer , catalysis , copolymer , geotechnical engineering , fracture (geology) , engineering
3‐Acylimino‐1‐methylbenzimidazolium betaines undergo 1,3‐dipolar cycloaddition reactions with activated alkenes (methyl acrylate, acrylonitrile, and fumaronitrile) and methyl propiolate to produce 2‐substituted 1‐methylbenzimidazoles. The transformation involves the initial formation of a 1,3‐dipolar cycloadduct followed by the NN bond cleavage. The primary adducts can be isolated from the reaction with methyl acrylate and acrylonitrile.