Modular Synthesis of Tetrasubstituted Pyrroles through a Four-Component Cyclization Strategy Using Ammonium Salt as the Nitrogen Source

Chunlan Zhou; Haolin Zheng; Ya Chen; Guojiang Mao; Guo-Jun Deng

doi:10.1021/acs.joc.2c02556

Modular Synthesis of Tetrasubstituted Pyrroles through a Four-Component Cyclization Strategy Using Ammonium Salt as the Nitrogen Source

J Org Chem. 2023 Feb 3;88(3):1533-1544. doi: 10.1021/acs.joc.2c02556. Epub 2023 Jan 18.

Authors

Chunlan Zhou¹, Haolin Zheng¹, Ya Chen¹, Guojiang Mao², Guo-Jun Deng¹

Affiliations

¹ Key Laboratory for Green Organic Synthesis and Application of Hunan Province, Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105, PR China.
² School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, PR China.

PMID: 36655334
DOI: 10.1021/acs.joc.2c02556

Abstract

A four-component synthesis of tetrasubstituted pyrroles was developed under metal-free conditions. The pyrrole ring was formed in one pot through [2 + 1 + 1 + 1] condensation using ammonium salt as the nitrogen source. In this strategy, 1,4-naphthoquinones and maleimides were used as the versatile C2 fragments to provide substituted benzo[f]isoindole-4,9-diones and pyrrolo[3,4-c]pyrrole-1,3-diones, respectively. This work is highlighted by using ammonium salt as the nitrogen source, readily available starting materials and multibond formation (two C-C and two C-N bonds) in a single operation.