Iminophosphoranes in heterocyclic chemistry.: A simple one-pot synthesis of pyridothienopyridazines and pyrimidothienopyridazines

被引：26

作者：

Alvarez-Sarandés, R ^{[1
]}

Peinador, C ^{[1
]}

Quintela, JM ^{[1
]}

机构：

[1] Univ A Coruna, Fac Ciencias, Dept Quim Fundamental, E-15071 La Coruna, Spain

来源：

TETRAHEDRON | 2001年 / 57卷 / 25期

关键词：

iminophosphorane; aza-Wittig; pyridothienopiridazine; pyrimidothienopyridazine;

D O I：

10.1016/S0040-4020(01)00460-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Iminophosphoranes, 6-(2-ethoxycarbonylvinyl)-3,4-diphenyl-5-[(triphenylphosphoranylidene)amino]thieno[2,3-c]pyridazine la, 6-(2-cyanovinyl)-3,4-diphenyl-5-[(triphenylphosphoranylidene)amino]thieno [2,3-c]pyridazine Ib, and 6-(4-aryliminomethylene)-3,4-diphenyl-5-[(triphenylphosphoranylidene)amino]thieno[2,3-c] pyridazine 5a-c react with heterocumulenes such as iso(thio)cyanates, carbon dioxide and carbon disulfide to give directly the title compounds in an aza-Wittig/electrocyclic-ring closure process. The N-heteroaryliminophosphoranes 8a,b underwent an unusual pyridine ring closure under Vilsmeier conditions to form the pyridothienopyridazines 10a,b. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：5413 / 5420

页数：8

共 47 条

[41] SYNTHESIS OF NOVEL CARBOPOLYCYCLES AND HETEROPOLYCYCLES .12. A NEW VERSATILE SYNTHESIS OF OXAZOLES BY INTRAMOLECULAR AZA-WITTIG REACTION [J].

TAKEUCHI, H ;

YANAGIDA, S ;

OZAKI, T ;

HAGIWARA, S ;

EGUCHI, S .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (02) :431-434

[42] A NEW EFFICIENT SYNTHESIS OF IMIDAZOLINONES AND QUINAZOLINONE BY INTRAMOLECULAR AZA-WITTIG REACTION [J].

TAKEUCHI, H ;

HAGIWARA, S ;

EGUCHI, S .

TETRAHEDRON, 1989, 45 (20) :6375-6386

[43]

Tisler M, 1990, ADV HETEROCYCLIC CHE, V49, P385

[44]

Veiga MC, 1996, HETEROCYCLES, V43, P1073

[45] ON THE SYNTHESIS OF ZWITTERIONIC HETEROPOLYCYCLIC PYRAZOLES BY A 3-COMPONENT REACTION - SOME MECHANISTIC CONSIDERATIONS [J].

WAMHOFF, H ;

BAMBERG, C ;

HERRMANN, S ;

NIEGER, M .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (14) :3985-3993

[46] REACTIONS OF URACILS .21. ZWITTERIONIC HETEROPOLYCYCLIC URACILS BY A NOVEL 3-COMPONENT REACTION - IMINOPHOSPHORANE, ISOCYANATE, HETEROARENE [J].

WAMHOFF, H ;

SCHMIDT, A .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (25) :6976-6984

[47]

Wamhoff H., 1995, ADV HETEROCYCL CHEM, V64, P159

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