A CONVENIENT PREPARATION OF [1,2,4]TRIAZOLO[1,5-A]PYRIDINES FROM ACETOHYDRAZIDE DERIVATIVES - SYNTHETIC AND MECHANISTIC ASPECTS

被引：18

作者：

CALLEJO, MJ ^{[1
]}

LAFUENTE, P ^{[1
]}

MARTINLEON, N ^{[1
]}

QUINTEIRO, M ^{[1
]}

SEOANE, C ^{[1
]}

SOTO, JL ^{[1
]}

机构：

[1] UNIV COMPLUTENSE MADRID,FAC QUIM,DEPT QUIM ORGAN,E-28040 MADRID,SPAIN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1990年 / 06期

关键词：

D O I：

10.1039/p19900001687

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel synthesis of triazolo[1,5-a]pyridines (4) from 2′-acetyl-2-cyanoacetohydrazide (2) and arylidenemalononitriles (3) is described. The synthesis can be carried out either in one step or via 1-acetamidopyridones (5). Alternatively, acetylation of 1-aminopyridones (7) also gives triazolo[1,5-a]pyridines (4). Reaction of (2) with (3) in the presence of piperidine leads to the piperidinium salt of the triazolo[1,5-a]pyridine (6), which can be neutralized to give (4).

引用

页码：1687 / 1690

页数：4

共 22 条

[1] N-AMINO-2-PYRIDONES FROM ACETOHYDRAZIDE DERIVATIVES [J].

APARICIO, C ;

MARTIN, N ;

QUINTEIRO, M ;

SEOANE, C ;

SOTO, JL ;

VALDES, JA ;

VELAZQUEZ, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (11) :1975-1979

[2]

BUELL BG, 1836, Patent No. 327281

[3] SEARCH FOR COMPOUNDS WHICH HAVE AN INHIBITORY EFFECT ON RHABDOVIRUS MULTIPLICATION INVITRO [J].

BUSSEREAU, F ;

CHERMANN, JC ;

DECLERCQ, E ;

HANNOUN, C .

ANNALES DE VIROLOGIE, 1983, 134 (01) :127-134

[4]

CAREY L, 1982, Patent No. 48555

[5]

CHUIGUK VA, 1980, UKR KHIM ZH, V46, P1306

[6]

Cope A. C., 1941, J AM CHEM SOC, V63, P733

[7] Reactions of alpha, beta-unsaturated dinitriles [J].

Corson, BB ;

Stoughton, RW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1928, 50 :2825-2837

[8] SYNTHESIS OF AMINOPYRAZOLOPYRIDINES AND AMINOTRIAZOLO[2,3-A]PYRIDINES [J].

GEWALD, K ;

SCHUBERT, A ;

MARTIN, G .

JOURNAL FUR PRAKTISCHE CHEMIE, 1975, 317 (04) :561-566

[9]

Irikura T., 1980, French Patent, Patent No. [2,450,259, 2450259]

[10]

Irikura T., 1980, German Patent, Patent No. [2,905,823, 2905823]

← 1 2 3 →