Issue 29, 2020
From the journal:

Organic & Biomolecular Chemistry

Facile access to N-formyl imide as an N-formylating agent for the direct synthesis of N-formamides, benzimidazoles and quinazolinones†

Hsin-Yi Huang,‡a   Xiu-Yi Lin,‡a   Shih-Yao Yena  and  Chien-Fu Liang ORCID logo *a  

* Corresponding authors

a Department of Chemistry, National Chung Hsing University, Taichung, Taiwan
E-mail: lcf0201@dragon.nchu.edu.tw
Tel: +886-4-22840411

Abstract

N-Formamide synthesis using N-formyl imide with primary and secondary amines with catalytic amounts of p-toluenesulfonic acid monohydrate (TsOH·H2O) is described. This reaction is performed in water without the use of surfactants. Moreover, N-formyl imide is efficiently synthesized using acylamidines with TsOH·H2O in water. In addition, N-formyl imide was successfully used as a carbonyl source in the synthesis of benzimidazole and quinazolinone derivatives. Notable features of N-formylation of amines by using N-formyl imide include operational simplicity, oxidant- and metal-free conditions, structurally diverse products, and easy applicability to gram-scale operation.

Graphical abstract: Facile access to N-formyl imide as an N-formylating agent for the direct synthesis of N-formamides, benzimidazoles and quinazolinones

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Article information

DOI
https://doi.org/10.1039/D0OB01080D
Article type
Paper
Submitted
25 May 2020
Accepted
03 Jul 2020
First published
06 Jul 2020

Org. Biomol. Chem., 2020,18, 5726-5733

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Facile access to N-formyl imide as an N-formylating agent for the direct synthesis of N-formamides, benzimidazoles and quinazolinones

H. Huang, X. Lin, S. Yen and C. Liang, Org. Biomol. Chem., 2020, 18, 5726 DOI: 10.1039/D0OB01080D

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