Your browser doesn't support javascript.
loading
Nickel(II)-Catalyzed Formal [3+2] Cycloadditions between Indoles and Donor-Acceptor Cyclopropanes.
Quezada, Víctor; Castroagudín, Mariña; Verdugo, Felipe; Ortiz, Sergio; Zaragoza, Guillermo; Nachtigall, Fabiane M; Reis, Francisco A A; Castro-Alvarez, Alejandro; Santos, Leonardo S; Nelson, Ronald.
Afiliação
  • Quezada V; Departamento de Química, Facultad de Ciencias, Universidad Católica del Norte, Avda. Angamos 0610, Antofagasta 1270709, Chile.
  • Castroagudín M; Departamento de Química, Facultad de Ciencias, Universidad Católica del Norte, Avda. Angamos 0610, Antofagasta 1270709, Chile.
  • Verdugo F; Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad de Concepción, Edmundo Larenas 129, Concepción 4070371, Chile.
  • Ortiz S; UMR 7200 Laboratoire d'Innovation Thérapeutique, CNRS, Strasbourg Drug Discovery and Development Institute (IMS), Université de Strasbourg, 67400 Illkirch-Graffenstaden, France.
  • Zaragoza G; Unidade de Difracción de Raios X, RIAIDT, Universidade de Santiago de Compostela, Campus VIDA, 15782 Santiago de Compostela, Spain.
  • Nachtigall FM; Instituto de Ciencias Aplicadas, Universidad Autónoma de Chile, Talca 3467987, Chile.
  • Reis FAA; Laboratory of Asymmetric Synthesis, Chemistry Institute of Natural Resources, Universidad de Talca, Talca 3460000, Chile.
  • Castro-Alvarez A; Departamento de Ciencias Preclínicas, Facultad de Medicina, Universidad de La Frontera, Temuco 4811230, Chile.
  • Santos LS; Laboratory of Asymmetric Synthesis, Chemistry Institute of Natural Resources, Universidad de Talca, Talca 3460000, Chile.
  • Nelson R; Departamento de Química, Facultad de Ciencias, Universidad Católica del Norte, Avda. Angamos 0610, Antofagasta 1270709, Chile.
Molecules ; 29(7)2024 Apr 03.
Article em En | MEDLINE | ID: mdl-38611883
ABSTRACT
This article describes the development of a nickel-catalyzed regio- and diastereoselective formal [3+2] cycloaddition between N-substituted indoles and donor-acceptor cyclopropanes to synthesize cyclopenta[b]indoles. Optimized reaction conditions provide the desired nitrogen-containing cycloadducts in up to 93% yield and dr 8.61 with complete regioselectivity. The substrate scope showed high tolerance to various substituted indoles and cyclopropanes, resulting in the synthesis of six new cyclopenta[b]indoles and the isolation of five derivatives previously reported in the literature. In addition, a mechanistic proposal for the reaction was studied through online reaction monitoring by ESI-MS, allowing for the identification of the reactive intermediates in the Ni(II) catalyzed process. X-ray crystallography confirmed the structure and relative endo stereochemistry of the products. This method enables the fast and efficient construction of fused indolines from readily accessible starting materials.
Palavras-chave
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: Molecules Assunto da revista: BIOLOGIA Ano de publicação: 2024 Tipo de documento: Article País de afiliação: Chile País de publicação: Suíça
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: Molecules Assunto da revista: BIOLOGIA Ano de publicação: 2024 Tipo de documento: Article País de afiliação: Chile País de publicação: Suíça