Facile access to N-formyl imide as an N-formylating agent for the direct synthesis of N-formamides, benzimidazoles and quinazolinones. Issue 29 (15th July 2020)

• Record Type: Journal Article
• Authors: Huang, Hsin-Yi; Lin, Xiu-Yi; Yen, Shih-Yao; Liang, Chien-Fu
• Is Part Of: Organic & biomolecular chemistry. Volume 18:Issue 29(2020)
• Page Start: 5726
• Page End: 5733
• Publication Date: 2020-07-15
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d0ob01080d
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : We developed a green method to produce N -formyl imides using acylamidines in water. Subsequently, N -formyl imide can be as a new water-tolerant N -formylating agent for the synthesis of N -formamides, benzimidazoles and quinazolinones. Abstract : N -Formamide synthesis using N -formyl imide with primary and secondary amines with catalytic amounts of p -toluenesulfonic acid monohydrate (TsOH·H2 O) is described. This reaction is performed in water without the use of surfactants. Moreover, N -formyl imide is efficiently synthesized using acylamidines with TsOH·H2 O 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.