Synthesis of 2,5‐Disubstituted Pyridines using the Gold(I)‐Catalyzed Cycloisomerization of 1‐Bromoalkynes as Key Step
Rubén Miguélez, Omar Arto, Carlos Rodríguez‐Arias, Ángel del Blanco, Pablo Barrio, José M. González
Abstract
Abstract Gold‐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.
Topics & Concepts
CycloisomerizationChemistryCatalysisPyridineBicyclic moleculeCombinatorial chemistryOrganic chemistryNatural productOzonolysisStereochemistryCatalytic Alkyne ReactionsTraditional and Medicinal Uses of Annonaceae