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Preparation of 3-(Fluoroalkyl)-2-azadienes and Its Application in the Synthesis of (Fluoroalkyl)isoquinoline and -pyridine Derivatives

✍ Scribed by Francisco Palacios; Concepción Alonso; Marta Rodríguez; Eduardo Martínez de Marigorta; Gloria Rubiales

Publisher: John Wiley and Sons
Year: 2005
Tongue: English
Weight: 161 KB
Volume: 2005
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.200400770

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✦ Synopsis

Abstract

A method for the preparation of 3‐(fluoroalkyl)‐substituted 2‐azabutadienes 5 by aza‐Wittig reaction of N‐vinylic 3‐(fluoroalkyl)phosphazenes 4 and aldehydes is reported. Thermal 6π‐electrocyclization of these azadienes gives 3‐(fluoroalkyl)‐substituted isoquinolines 6. Also [4+2] cycloaddition of these heterodienes 5 with enamine 8 gives fluoroalkyl‐substituted pyridine derivatives 10–16. However, the reaction of azadienes 17 with azo compound 18 affords bicyclic heterocycles 19. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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