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Homolytic Substitution and Carbenoidic Reactions in the Preparation of Benzimidazole Derivatives of Pharmaceutical Interest: Synthesis and Properties of (2‐Cycloalkyl‐1‐benzimidazolyl)‐ N,N ‐diethylacetamides
Author(s) -
Pellicciari Roberto,
Fringuelli Renata,
Natalini Benedetto,
Brucato Leonardo,
Contessa Anna Rita
Publication year - 1985
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19853180503
Subject(s) - homolysis , benzimidazole , chemistry , oxidative decarboxylation , alkylation , peroxydisulfate , organic chemistry , radical , heteroatom , medicinal chemistry , decarboxylation , combinatorial chemistry , catalysis , alkyl
Abstract The preparation and preliminary biological evaluation of the (2‐cycloalkyl‐1‐benzimidazolyl)‐N,N‐diethylacetamides 7a–e are described. Key steps for the preparation of the compounds 7a–d are (i) the homolytic cycloalkylation of benzimidazole, in which the silver‐catalyzed oxidative decarboxylation of the cycloalkanecarboxylic acids 1a–d by peroxydisulfate is used as a source of alkyl radicals, and (ii) the N ‐alkylation of benzimidazole by the ethoxycarbonylcarbenoid generated by the copper bronze‐catalyzed decomposition of ethyl diazoacetate.