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Aguilar et al. Chem Rev. 2016;116(14):8256-311. 1,3-Dien-5-ynes: Versatile Building Blocks for the Synthesis of Carbo- and Heterocycles.

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Chem Rev. 2016 Jul 27;116(14):8256-311. doi: 10.1021/acs.chemrev.6b00181.

1,3-Dien-5-ynes: Versatile Building Blocks for the Synthesis of Carbo- and Heterocycles.

Enrique Aguilar1, Roberto Sanz2, Manuel A Fernández-Rodríguez2, Patricia García-García3

1. Instituto Universitario de Química Organometálica "Enrique Moles", Departamento de Química Orgánica e Inorgánica, Universidad de Oviedo , C/Julián Clavería 8, 33006 Oviedo, Spain.  2. Departamento de Química, Área de Química Orgánica, Facultad de Ciencias, Universidad de Burgos , Pza. Misael Bañuelos s/n, 09001 Burgos, Spain.  3. Departamento de Química Orgánica y Química Inorgánica, Universidad de Alcalá , 28871 Alcalá de Henares, Madrid, Spain.

Abstract

1,3-Dien-5-ynes have been extensively used as starting materials for the synthesis of a wide number of different carbo- and heterocycles. The aim of this review is to give an overview of their utility in organic synthesis, highlighting the variety of compounds that can be directly accessed from single reactions over these systems. Thus, cycloaromatization processes are initially commented, followed by reactions directed toward the syntheses of five-membered rings, other carbocycles and, finally, heterocycles. The diverse methodologies that have been developed for the synthesis of each of these types of compounds from 1,3-dien-5-ynes are presented, emphasizing the influence of the reaction conditions and the use of additional reagents in the outcome of the transformations.