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

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-1 H -imidazol-3-ium iodide has been devel...

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Published inSynOpen (2017) Vol. 6; no. 2; pp. 132 - 140
Main Authors Jagadeesha, Gullahalli S., Mantelingu, Kempegowda, Thimmegowda, Naraganahalli R., Rangappa, Kanchugarakoppal S.
Format Journal Article
LanguageFrench
English
Published Rüdigerstraße 14, 70469 Stuttgart, Germany Georg Thieme Verlag KG 01.06.2022
Subjects
2-formyl-1,3-dimethyl-1h-imidazol-3-ium iodide
benzimidazole
isocyanide
microwave-assisted synthesis
n -formylation
n-formamide
microwave-assisted synthesis
imidazol-3-ium iodide
formylation
2-formyl-1,3-dimethyl-1
benzimidazole
formamide
isocyanide
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Summary: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-1 H -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.
ISSN:2509-9396
2509-9396
DOI:10.1055/s-0041-1737605