Journal
TETRAHEDRON
Volume 74, Issue 40, Pages 5932-5941Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2018.08.029
Keywords
N-Alkylation; Benzimidazole; Sodium dodecyl sulphate; Ring opening reaction; Aqueous medium
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Funding
- DST-SERB, Govt. of India [EMR/2016/001537]
- DST, Govt. of India
- DST-FIST fund [SR/FST/CS1-263/2015]
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A sustainable route for the N-1 alkylation of imidazole and benzimidazole derivatives has been developed under volatile organic solvent free condition in alkaline water-SDS system. Incorporation of SDS in the reaction medium enhances the reaction rate by suppressing the solubility issue that arises for different substrates. This method provides high yield of the alkylated product in a shorter reaction time. For reactive alkyl halides reaction proceeds at ambient temperature whereas in the cases of less reactive alkyl halides require 55-60 degrees C to complete alkylation process. N-alkylation induced ring opening of the heterocyclic ring in benzimidazole derivatives to multifunctional aromatic compounds were noticed at 60 degrees C when more than two equivalents of alkyl halide was used. (C) 2018 Elsevier Ltd. All rights reserved.
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