Aza-Wittig reaction of fluoroalkylated N-vinylic phosphazenes with carbonyl compounds.: Usefulness of 2-azadienes for the preparation of fluoroalkyl pyridine derivatives

被引：48

作者：

Palacios, F ^{[1
]}

Alonso, C ^{[1
]}

Rubiales, G ^{[1
]}

Villegas, M ^{[1
]}

机构：

[1] Univ Basque Country, Fac Farm, Dept Quim Organ 1, Bilbao 01080, Spain

来源：

TETRAHEDRON | 2005年 / 61卷 / 11期

关键词：

N-vinylic phosphazenes; aza-Wittig reaction; 2-aza-1; 3-butadienes; fluoroalkyl derivatives; heterocycles;

D O I：

10.1016/j.tet.2005.01.080

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for the preparation of 3-fluoroalkyl substituted 2-aza-butadienes 6 by aza-Wittig reaction of 3-fluoroalkyl-N-vinylic phosphazenes 4 and aldehydes 5 is reported. [4+2] Cycloaddition reaction of these heterodienes 6 with enamines 9 gives fluoroalkyl substituted pyridine 15, 16, 24-27 and isoquinoline 12-14, 20 derivatives. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：2779 / 2794

页数：16

共 9 条

[1] Aza-Wittig reaction of N-vinylic phosphazenes with carbonyl compounds. Azadiene-mediated synthesis of dihydropyridines and pyridines
Palacios, F
Rubiales, G
TETRAHEDRON LETTERS, 1996, 37 (35) : 6379 - 6382
[2] Aza-Wittig reaction of N-Vinylic phosphazenes with carbonyl compounds. Azadiene-mediated synthesis of dihydropyridines and pyridines
Tetrahedron Lett, 35 (6379):
[3] Reaction of N-vinylic phosphazenes with carbonyl compounds. Reactivity of the vinyl side chain versus Aza-Wittig reaction.
Palacios, F
Aparicio, D
delosSantos, JM
TETRAHEDRON, 1996, 52 (13) : 4857 - 4866
[4] Aza-Wittig Reaction of N-Vinylic Phosphazenes with Carbonyl Compounds. Azadiene-Mediated Synthesis of Isoquinolines and 5,6-Dihydro-2H-1,3-oxazines
Palacios, F.
Alonso, C.
Rubiales, G.
Journal of Organic Chemistry, 62 (04):
[5] Aza-Wittig reaction of N-vinylic phosphazenes with carbonyl compounds. Azadiene-mediated synthesis of isoquinolines and 5,6-dihydro-2H-1,3-oxazines
Palacios, F
Alonso, C
Rubiales, G
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (04): : 1146 - 1154
[6] A new and efficient synthesis of imidazo[1,5-a]pyridine derivatives by a tandem aza-Wittig/electrocyclic ring closure of N-vinylic phosphazenes
Palacios, F.
Alonso, C.
Rublales, G.
Textile Dyer and Printer, 1994, 27 (17):
[7] A NEW AND EFFICIENT SYNTHESIS OF IMIDAZO[1,5-A]PYRIDINE DERIVATIVES BY A TANDEM AZA-WITTIG ELECTROCYCLIC RING-CLOSURE OF N-VINYLIC PHOSPHAZENES
PALACIOS, F
ALONSO, C
RUBIALES, G
TETRAHEDRON, 1995, 51 (12) : 3683 - 3690
[8] Aza-Wittig reaction of N-phosphorylalkyl phosphazenes with carbonyl compounds and phenylisocyanate.: Synthesis of 4-amino-3-phosphoryl-2-azadienes and pyrazine-phosphonates
Palacios, F
de Retana, AMO
de Marigorta, EM
Rodriguez, M
Pagalday, J
TETRAHEDRON, 2003, 59 (15) : 2617 - 2623
[9] Cycloaddition reaction of 2-azadienes derived from β-amino acids with electron-rich and electron-deficient alkenes and carbonyl compounds.: Synthesis of pyridine and 1,3-oxazine derivatives
Palacios, F
Herrán, E
Rubiales, G
Ezpeleta, JM
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (07): : 2131 - 2135

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