6-PI-ELECTROCYCLIZATION OF AZAHEXA-1,3,5-TRIENES - A NEW ENTRY TO A REGIOSPECIFIC SYNTHESIS OF 3-ARYL(HETEROARYL)PYRIDINES

被引：41

作者：

MOLINA, P

PASTOR, A

VILAPLANA, MJ

机构：

[1] Departamento de Química Orgánica, Facultad de Química, Universidad de Murcia, E-30071 Murcia, Campus de Espinardo

来源：

TETRAHEDRON | 1993年 / 49卷 / 35期

关键词：

D O I：

10.1016/S0040-4020(01)87250-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aza Wittig reaction of iminophosphoranes derived from ethyl alpha-azido-beta-aryl(pyrazolyl)propenoates with alpha,beta-unsaturated aldehydes leads to aldimines which by heating undergo electrocyclic ring-closure through the 3-azahexa-1,3,5-triene moiety to give 3-aryl(pyrazolyl)pyridines in a completely regiospecific fashion. However, iminophosphoranes derived from ethyl alpha-azido-beta-furyl(thienyl)propenoates furnish a mixture (1.2:1 ratio) of the corresponding furo- or thieno-pyridine(2-azahexa-1,3,5-triene electrocyclization product) and 3-furyl(thienyl)pyridine(3-azahexa-1,3,5-triene electrocyclization product).

引用

页码：7769 / 7778

页数：10

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