Regioselective Synthesis of Polysubstituted Carbazoles from Indoles and Simple 1,4-Dicarbonyl Compounds

Author(s)

Santos, Hugo ; Zeoly, Lucas A. ; Rebechi, Rafael ; Arantes, Joao ; Coelho, Fernando ; Rodrigues Jr, Manoel T.

• Document type: Journal article
• Source: ADVANCED SYNTHESIS & CATALYSIS; v. 366, n. 4, p. 8-pg., 2024-02-21.

Abstract

Polysubstituted carbazoles were efficiently synthesized through direct benzannulation reaction between 1,4-dicarbonyl compounds and indoles with catalytic amount of inexpensive zirconium(IV) chloride. This transformation proved to be regioselective and furnishes 1,4-disubstituted and 1,2,4-trisubstituted carbazoles with yields ranging from 26% to 91% and broad substrate scope. Moreover, this protocol benefits from using readily accessible starting materials without the need of their pre-functionalization. The synthetic utility of the products was exemplified by functionalization of an iodocarbazole by means of Suzuki-Miyaura reactions and by the synthesis of a 3-deaza-derivative of the natural product canthin-6-one. image (AU)

• FAPESP's process: 15/09205-0 - New frontiers of the Morita-Baylis-Hillman reaction: 1) New applications of a bifunctional catalyst derived from imidazole. 2) Studies on the asymmetric synthesis of a natural high-potency sweetener
• Grantee: Hugo dos Santos
• Support Opportunities: Scholarships in Brazil - Doctorate (Direct)
• FAPESP's process: 13/07600-3 - CIBFar - Center for Innovation in Biodiversity and Drug Discovery
• Grantee: Glaucius Oliva
• Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC