Synthesis of Sulfamate-Fused 2-Aminopyrroles via an Isocyanide-Based Three Component [1+2+2] Annulation

Chuan-Chuan Wang; Zhi-Wei Ma; Ya-Li Qu; Zhi-Jing Liu; Xiao-Pei Chen; Jing Zhou; Ya-Jing Chen

doi:10.1002/asia.201901780

Synthesis of Sulfamate-Fused 2-Aminopyrroles via an Isocyanide-Based Three Component [1+2+2] Annulation

Chem Asian J. 2020 Mar 2;15(5):560-563. doi: 10.1002/asia.201901780. Epub 2020 Jan 23.

Authors

Chuan-Chuan Wang^{1

2}, Zhi-Wei Ma¹, Ya-Li Qu³, Zhi-Jing Liu¹, Xiao-Pei Chen¹, Jing Zhou³, Ya-Jing Chen³

Affiliations

¹ Faculty of Science, Henan University of Animal Husbandry and Economy, No. 2 Yingcai Street, Zhengzhou, 450044, Henan, P. R. China.
² College of Chemistry, Zhengzhou University, 100 Science Avenue, Zhengzhou, 450001, Henan, P. R. China.
³ School of Pharmaceutical Sciences, Key Laboratory of Advanced Drug Preparation Technologies, Ministry of Education of China, Co-innovation Center of Henan Province for New Drug R & D and Preclinical Safety, Zhengzhou University, 100 Science Avenue, Zhengzhou, 450001, Henan, P. R. China.

PMID: 31903670
DOI: 10.1002/asia.201901780

Abstract

An efficient preparation of sulfamate-fused 2-aminopyrroles was achieved through an isocyanide-based three-component [1+2+2] annulation of isocyanides, dialkyl acetylenedicarboxylates, and sulfamate-derived cyclic imines in good to excellent yields (up to 99 %). This reaction proceeds smoothly without any activation or modification of substances under neutral and metal-free conditions. The reaction could also be conveniently performed on a gram scale.

Keywords: annulation; imines; isocyanide-based multicomponent reactions (IMCRs); sulfamate-fused pyrroles.

Abstract

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