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DOI: 10.1055/s-0041-1737605
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
Financial support from the Vision Group on Science and Technology, Government of Karnataka (No. VGST/SMYSR/GRD-426) is gratefully acknowledged.
![](https://www.thieme-connect.de/media/10.1055-s-00032269/202202/lookinside/thumbnails/so-2022-d0011-op_10-1055_s-0041-1737605-1.jpg)
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 - benzimidazoleSupporting 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. The Author(s). 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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