Synthesis of 9,10‐Bis(organochalcogenyl)phenanthrenes by Cyclization of (Biphenyl‐2‐alkyne)chalcogenides

Author:

Hellwig Paola S.1ORCID,Goulart Helen A.1ORCID,Guedes Jonatan S.1ORCID,Jorge Emily G.1,Barcellos Angelita M.2ORCID,Lenardão Eder J.1ORCID,Perin Gelson1ORCID

Affiliation:

1. Centro de Ciências Químicas Farmacêuticas e de Alimentos – CCQFA Universidade Federal de Pelotas – UFPel P. O. box 354, CEP 96010-900 Pelotas RS Brazil

2. Escola de Química e Alimentos Universidade Federal do Rio Grande – FURG CEP 96203-900 Rio Grande RS Brazil.

Abstract

AbstractA regioselective, operationally simple and scalable protocol was developed for the synthesis of 9,10‐bis(organochalcogenyl)phenanthrenes and seleno‐spiro[cyclohexane‐1,1′‐indene]‐2,5‐dien‐4‐ones through the cyclization of (biphenyl‐2‐alkyne)chalcogenides. The reaction occurs in the presence of diorganyl diselenides, Oxone® as a green oxidizing agent, and acetonitrile at 80 °C. In this study, 20 compounds were obtained in yields of up to 97 % and in short reaction times (1–4 h).

Funder

Conselho Nacional de Desenvolvimento Científico e Tecnológico

Financiadora de Estudos e Projetos

Publisher

Wiley

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