TRIAZOLOPYRIDINES .16. LITHIATION OF 3-CYANO[1,2,3]TRIAZOLO[1,5-A]-PYRIDINE

被引：11

作者：

JONES, G ^{[1
]}

MOUAT, DJ ^{[1
]}

PITMAN, MA ^{[1
]}

LUNT, E ^{[1
]}

LYTHGOE, DJ ^{[1
]}

机构：

[1] RHONE POULENC RORER LTD,DAGENHAM RES CTR,DAGENHAM RM10 7XS,ESSEX,ENGLAND

来源：

TETRAHEDRON | 1995年 / 51卷 / 40期

关键词：

D O I：

10.1016/0040-4020(95)00652-O

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Various methods for the synthesis of 3-cyanotriazolopyridine 8 by diazo transfer to 2-pyridylacetonitrile are described. Lithiation of the triazolopyridine 8 using LDA or TMPA followed by quenching with TMS chloride, gave the 4-mono-, the 7-mono-,and the 4,7- di TMS derivatives 14, 18, and 15, and the amidines 16 and 17, in contrast to the previously reported regiospecific attack at position 7. A Grignard reaction on compound 8 gave 3-propionyl triazolopyridine, 13.

引用

页码：10969 / 10978

页数：10

共 8 条

[1] TRIAZOLOPYRIDINES .7. PREPARATION OF BROMO-TRIAZOLOPYRIDINES AND BROMO-TRIAZOLOISOQUINOLINES [J].

ABARCA, B ;

BALLESTEROS, R ;

MOJARRED, F ;

JONES, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (08) :1865-1868

[2]

ABARCA B, 1983, J CHEM RES-S, P144

[3]

ABARCA B, 1993, HETEROCYCLES, V35, P851

[4] DIAZO-GROUP TRANSFER TO ACTIVE METHYLENE-COMPOUNDS USING AZIDINIUM SALTS [J].

BALLI, H ;

LOW, R ;

MULLER, V ;

REMPFLER, H ;

SEZENGEZGIN, A .

HELVETICA CHIMICA ACTA, 1978, 61 (01) :97-103

[5]

DARR JA, 1993, INORG CHEM, P5704

[6] TRIAZOLOPYRIDINES .2. PREPARATION OF 7-SUBSTITUTED TRIAZOLO[1,5-A]PYRIDINES BY DIRECTED LITHIATION [J].

JONES, G ;

SLISKOVIC, DR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (04) :967-971

[7] PREPARATION OF ALPHA-DIAZO-BETA-KETOSULFONES BY DIAZO-TRANSFER REACTION WITH AN INSITU GENERATED AZIDINIUM SALT - A SAFE AND EFFICIENT PROCEDURE FOR THE DIAZO-TRANSFER REACTION IN NEUTRAL MEDIUM [J].

MONTEIRO, HJ .

SYNTHETIC COMMUNICATIONS, 1987, 17 (08) :983-992

[8] REAKTIONEN AKTIVER METHYLENVERBINDUNGEN MIT AZIDEN .11. SYNTHESE VON NU-TRIAZOLO[3.4-ALPHA]PYRIDINEN UND -CHINOLINEN DURCH DIAZOGRUPPENUBERTRAGUNG [J].

REGITZ, M .

CHEMISCHE BERICHTE-RECUEIL, 1966, 99 (09) :2918-&

← 1 →