Copper-Mediated Intramolecular Interrupted CuAAC Selanylation.

Teixeira, Wystan K O; de Albuquerque, Danilo Yano; Zukerman-Schpector, Julio; Seckler, Diego; Rampon, Daniel S; Schwab, Ricardo S

Teixeira, Wystan K O; de Albuquerque, Danilo Yano; Zukerman-Schpector, Julio; Seckler, Diego; Rampon, Daniel S; Schwab, Ricardo S.

Afiliação

Teixeira WKO; Centre of Excellence for Research in Sustainable Chemistry (CERSusChem), Departamento de Química, Universidade Federal de São Carlos - UFSCar, Rodovia Washington Luís, km 235 - SP-310, São Carlos 13565-905, São Paulo, Brazil.
de Albuquerque DY; Centre of Excellence for Research in Sustainable Chemistry (CERSusChem), Departamento de Química, Universidade Federal de São Carlos - UFSCar, Rodovia Washington Luís, km 235 - SP-310, São Carlos 13565-905, São Paulo, Brazil.
Zukerman-Schpector J; Departamento de Química, Universidade Federal de São Carlos - UFSCar, Rodovia Washington Luís, km 235 - SP-310, São Carlos 13565-905, São Paulo, Brazil.
Seckler D; Laboratory of Polymers and Catalysis (LaPoCa), Departamento de Química, Universidade Federal do Paraná - UFPR, P. O. Box 19061, Curitiba 81531-980, Paraná, Brazil.
Rampon DS; Laboratory of Polymers and Catalysis (LaPoCa), Departamento de Química, Universidade Federal do Paraná - UFPR, P. O. Box 19061, Curitiba 81531-980, Paraná, Brazil.
Schwab RS; Centre of Excellence for Research in Sustainable Chemistry (CERSusChem), Departamento de Química, Universidade Federal de São Carlos - UFSCar, Rodovia Washington Luís, km 235 - SP-310, São Carlos 13565-905, São Paulo, Brazil.

J Org Chem ; 88(15): 10434-10447, 2023 Aug 04.

Article em En | MEDLINE | ID: mdl-37467464

RESUMO

We, herein, describe a copper-mediated domino CuAAC intramolecular selanylation for the synthesis of unprecedented fused benzo[4,5][1,3]selenazolo[3,2-c][1,2,3]triazoles from 1,2-bis(2-azidoaryl)diselenides and terminal alkynes under microwave irradiation. This is the seminal method for the synthesis of these fused heterocycles, and it proceeds under mild conditions, tolerates several functional groups, and can be carried out using environmentally benign solvents such as dimethyl carbonate. This transformation has been successfully extended to TMS-protected alkynes and to bioactive alkynes. A plausible reaction mechanism is proposed based on several control experiments and previous reports.

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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: J Org Chem Ano de publicação: 2023 Tipo de documento: Article País de afiliação: Brasil País de publicação: Estados Unidos

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