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

Autor(es)

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

• Tipo de documento: Artigo Científico
• Fonte: ADVANCED SYNTHESIS & CATALYSIS; v. 366, n. 4, p. 8-pg., 2024-02-21.

Resumo

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)

• Processo FAPESP: 15/09205-0 - Novas fronteiras da reação de Morita-Baylis-Hillman: 1) Novas aplicações de um catalisador bifuncional derivado do imidazol. 2) Estudos visando à síntese assimétrica de um adoçante natural com alto potencial dulcífero
• Beneficiário: Hugo dos Santos
• Modalidade de apoio: Bolsas no Brasil - Doutorado Direto
• Processo FAPESP: 13/07600-3 - CIBFar - Centro de Inovação em Biodiversidade e Fármacos
• Beneficiário: Glaucius Oliva
• Modalidade de apoio: Auxílio à Pesquisa - Centros de Pesquisa, Inovação e Difusão - CEPIDs