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Photocatalyzed Intramolecular [2+2] Cycloaddition of N-Alkyl-N-(2-(1-arylvinyl)aryl)cinnamamides.
de Souza, Wanderson C; Matsuo, Bianca T; Matos, Priscilla M; Correia, José Tiago M; Santos, Marilia S; König, Burkhard; Paixão, Marcio W.
Afiliação
  • de Souza WC; Department of Chemistry, Federal University of São Carlos-UFSCar, Centre of Excellence for Research in Sustainable Chemistry, (CERSusChem), São Carlos, São Paulo, Brazil.
  • Matsuo BT; Department of Chemistry, Federal University of São Carlos-UFSCar, Centre of Excellence for Research in Sustainable Chemistry, (CERSusChem), São Carlos, São Paulo, Brazil.
  • Matos PM; Department of Chemistry, Federal University of São Carlos-UFSCar, Centre of Excellence for Research in Sustainable Chemistry, (CERSusChem), São Carlos, São Paulo, Brazil.
  • Correia JTM; Department of Chemistry, Federal University of São Carlos-UFSCar, Centre of Excellence for Research in Sustainable Chemistry, (CERSusChem), São Carlos, São Paulo, Brazil.
  • Santos MS; Department of Chemistry, Federal University of São Carlos-UFSCar, Centre of Excellence for Research in Sustainable Chemistry, (CERSusChem), São Carlos, São Paulo, Brazil.
  • König B; Institut für Organische Chemie, Universität Regensburg, Universitätsstrasse 31, 93053, Regensburg, Germany.
  • Paixão MW; Institut für Organische Chemie, Universität Regensburg, Universitätsstrasse 31, 93053, Regensburg, Germany.
Chemistry ; 27(11): 3722-3728, 2021 Feb 19.
Article em En | MEDLINE | ID: mdl-32955792
N-Alkyl-N-(2-(1-arylvinyl)aryl)cinnamamides are converted into natural product inspired scaffolds via iridium photocatalyzed intramolecular [2+2] photocycloaddition. The protocol has a broad substrate scope, whilst operating under mild reaction conditions. Tethering four components forming a trisubstituted cyclobutane core builds rapidly high molecular complexity. Our approach allows the design and synthesis of a variety of tetrahydrocyclobuta[c]quinolin-3(1H)-ones, in yields ranging between 20-99 %, and with excellent regio- and diastereoselectivity. Moreover, it was demonstrated that the intramolecular [2+2]-cycloaddition of 1,7-enynes-after fragmentation of the cyclobutane ring-leads to enyne-metathesis-like products.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: Chemistry Assunto da revista: QUIMICA Ano de publicação: 2021 Tipo de documento: Article País de afiliação: Brasil País de publicação: Alemanha
Texto completo
Adicionar na Minha BVS
Imprimir
XML
PubMed Links
Buscar no Google

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: Chemistry Assunto da revista: QUIMICA Ano de publicação: 2021 Tipo de documento: Article País de afiliação: Brasil País de publicação: Alemanha