Synthesis of 2,5‐Disubstituted Pyridines using the Gold(I)‐Catalyzed Cycloisomerization of 1‐Bromoalkynes as Key Step

Author:

Miguélez Rubén1,Arto Omar1,Rodríguez‐Arias Carlos1,del Blanco Ángel1,Barrio Pablo1ORCID,González José M.1

Affiliation:

1. Departamento de Química Orgánica e Inorgánica Instituto Universitario de Química Organometálica “Enrique Moles” Julian Clavería 8 33006 Oviedo Spain

Abstract

AbstractGold‐catalyzed cycloisomerization reaction of 1‐bromoalkynes allowed for the preparation of a variety of 1‐bromocyclopentene derivatives. These have been used as substrates in a 3‐step synthetic sequence comprising a cross‐coupling reaction, followed by ozonolysis, and final condensation towards the corresponding 2,5‐disubstituted pyridine. In addition, bicyclic fused pyridines are achieved, including the first total synthesis of the natural product Sinensine B.

Publisher

Wiley

Subject

Organic Chemistry,Physical and Theoretical Chemistry

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