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Syntheses and properties of 3‐acylimino‐1‐alkylimidazolium and benzimidazolium betaines
Author(s) -
Tamura Yasumitsu,
Hayashi Hironori,
Minamikawa JunIchi,
Ikeda Masazumi
Publication year - 1974
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.5570110522
Subject(s) - chemistry , benzamide , betaine , medicinal chemistry , alkyl , amine gas treating , thermal decomposition , cleavage (geology) , deuterium , hydrogen–deuterium exchange , bond cleavage , hydrogen bond , organic chemistry , molecule , hydrogen , catalysis , physics , geotechnical engineering , quantum mechanics , fracture (geology) , engineering
3‐Amino‐1‐alkylimidazolium and benzimidazolium mesitylenesulfonates were readily prepared in good to high yeilds by treating the parent heterocycles with O ‐mesitylenesulfonylhydroxylamine. Treatment of the 3‐amine salts with acylating agents gave crystalline 3‐acylimines, which showed the characteristic ir, uv, nmr, and mass spectral properties. Deuterium exchange of the 3‐acylimines occurs at the 2‐position. Thermolysis of neat 3‐benzoylimino‐1‐rnethylbenzimidazolium betaine afforded 2‐benzamido‐1‐methylbenzimidazole and products derived from NN bond cleavage. Irradiation of 3‐benzoylimino‐1‐alkylbenzimidazoliurn betaines resulted in NN bond cleavage to give 1‐alkylbenzimidazoles and benzamide, while the corresponding 3‐ethoxycarbonylimines underwent rearrangement to afford ethyl 1‐alkyl‐2‐benzimidazolecarbamates.