Cobalt-mediated macrocyclizations. Facile synthesis of 2-oxo pyridinophanes via [2 + 2 + 2] cycloaddition of alpha, omega-diynes and isocyanates

Llorente V R Boñaga; Han-Cheng Zhang; Diane A Gauthier; Indrasena Reddy; Bruce E Maryanoff

doi:10.1021/ol030096c

Cobalt-mediated macrocyclizations. Facile synthesis of 2-oxo pyridinophanes via [2 + 2 + 2] cycloaddition of alpha, omega-diynes and isocyanates

Org Lett. 2003 Nov 27;5(24):4537-40. doi: 10.1021/ol030096c.

Authors

Llorente V R Boñaga¹, Han-Cheng Zhang, Diane A Gauthier, Indrasena Reddy, Bruce E Maryanoff

Affiliation

¹ Drug Discovery, Johnson & Johnson Pharmaceutical Research & Development, Spring House, Pennsylvania 19477-0776, USA.

PMID: 14627377
DOI: 10.1021/ol030096c

Abstract

[reaction: see text] Cobalt-mediated [2 + 2 + 2] cycloaddition of alpha,omega-diynes and isocyanates provides a direct approach to macrocyclic 2-oxopyridinophanes. This macrocyclization process, which proceeded most efficiently with aliphatic isocyanates, was conveniently performed at a moderate temperature (85 degrees C) without irradiation or syringe-pump addition.