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Preparation of 3‐(Fluoroalkyl)‐2‐azadienes and Its Application in the Synthesis of (Fluoroalkyl)isoquinoline and ‐pyridine Derivatives
Author(s) -
Palacios Francisco,
Alonso Concepción,
Rodríguez Marta,
Martínez de Marigorta Eduardo,
Rubiales Gloria
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400770
Subject(s) - isoquinoline , chemistry , pyridine , cycloaddition , bicyclic molecule , wittig reaction , enamine , organic chemistry , combinatorial chemistry , medicinal chemistry , catalysis
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)