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

Palacios Francisco | Zendy; Alonso Concepción | Zendy; Rodríguez Marta | Zendy; Martínez de Marigorta Eduardo | Zendy; Rubiales Gloria | Zendy

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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

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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