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CC BY-NC-ND 4.0 · SynOpen 2022; 06(02): 132-140
DOI: 10.1055/s-0041-1737605
paper

Microwave-Assisted, Metal-Free, Chemoselective N-Formylation of Amines using 2-Formyl-1,3-dimethyl-1H-imidazol-3-ium Iodide and In Situ Synthesis of Benzimidazole and Isocyanides

Gullahalli S. Jagadeesha
a   Government S K S J Technological Institute, Affiliated to Visvesvaraya Technological University, K R Circle, Bangalore-560001, Karnataka, India
,
Kempegowda Mantelingu 
b   Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru-570006, Karnataka, India
,
Naraganahalli R. Thimmegowda  ∗
a   Government S K S J Technological Institute, Affiliated to Visvesvaraya Technological University, K R Circle, Bangalore-560001, Karnataka, India
,
Kanchugarakoppal S. Rangappa∗
c   Institution of Excellence, University of Mysore, Manasagangotri, Mysore-570006, Karnataka, India
› Author AffiliationsFinancial support from the Vision Group on Science and Technology, Government of Karnataka (No. VGST/SMYSR/GRD-426) is gratefully acknowledged.
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Microwave-Assisted, Metal-Free, Chemoselective N-Formylation of Amines using 2-Formyl-1,3-dimethyl-1H-imidazol-3-ium Iodide and In Situ Synthesis of Benzimidazole and IsocyanidesSynOpen 2022; 06(02): e1-e1
DOI: 10.1055/s-0040-1720034

Abstract

An efficient, environmentally benign, chemoselective, microwave-assisted N-formylation protocol of aromatic, aliphatic, alicyclic, benzylic amines, inactivated aromatic amines and sterically demanding heterocyclic amines using 2-formyl-1,3-dimethyl-1H-imidazol-3-ium iodide has been developed. This affords a series of N-substituted formamides with good to excellent yields (23 examples, 53–96% yield) and can be readily scaled. The methodology can be further extended to synthesize benzimidazole and isocyanide derivatives.

Key words

N -formylation - N-formamide - microwave-assisted synthesis - 2-formyl-1,3-dimethyl-1H-imidazol-3-ium iodide - isocyanide - benzimidazole

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0041-1737605. Included are the synthetic procedure for the synthesis of formylating agent 2 as well as 1H NMR, 13C NMR, LCMS, HRMS data for formylating agent 2 and final compounds 3a–p, 5a–g, 6a, 6b and 6c.
  • Supporting Information


Publication History

Received: 20 March 2022

Accepted after revision: 27 April 2022

Article published online:
08 June 2022

© 2022. This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

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