A convenient synthesis of pyridine and 2,2′-bipyridine derivatives

被引：29

作者：

Altuna-Urquijo, Marta ^{[1
]}

Gehre, Alexander ^{[1
]}

Stanforth, Stephen P. ^{[1
]}

Tarbit, Brian ^{[2
]}

机构：

[1] Northumbria Univ, Sch Appl Sci, Newcastle Upon Tyne NE1 8ST, Tyne & Wear, England

[2] Vertellus Special UK Ltd, Middlesbrough TS2 1UB, Cleveland, England

来源：

TETRAHEDRON | 2009年 / 65卷 / 05期

关键词：

Pyridines; 2,2 '-Bipyridines; 1,2,4-Triazines; alpha; beta-Diketo-esters; Aza Diels-Alder reaction; SIMPLE LEGO SYSTEM; DIELS-ALDER REACTIONS; HIGHLY SUBSTITUTED PYRIDINES; ONE-POT SYNTHESIS; BUILDING-BLOCKS; ALLYLIC OXIDATION; 1,2,4-TRIAZINES; LIGANDS; METHODOLOGY; COMPLEXES;

D O I：

10.1016/j.tet.2008.11.090

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-Chloro-alpha-acetoxy-beta-keto-esters 9 were readily prepared from beta-keto-esters 6 in good overall yields. These compounds reacted as alpha,beta-diketo-ester equivalents 2 with amidrazones 1 yielding triazines 3, generally in good yields. Picolinates 10 provided an alternative source of alpha,beta-diketo-ester equivalents 2 when treated with copper(II) acetate. A 'one-pot' reaction of the alpha,beta-diketo-ester equivalents 2 with amidrazones 1 in the presence of 2,5-norbornadiene 5 in boiling ethanol yielded the pyridines 4 and 2,2'-bipyridines 4 (R-1=2-pyridyl) directly without the need to isolate the corresponding triazines 3. Triazine 3c reacted with the aza-dienophiles 13 and 17 affording the products 16 and 18, respectively, in good yields. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：975 / 984

页数：10

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