An investigation into the alkylation of 1,2,4-triazole

被引：38

作者：

Bulger, PG ^{[1
]}

Cottrell, IF ^{[1
]}

Cowden, CJ ^{[1
]}

Davies, AJ ^{[1
]}

Dolling, UH ^{[1
]}

机构：

[1] Merck Sharp & Dohme Res Labs, Dept Proc Res, Hoddesdon EN11 9BU, Herts, England

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 08期

关键词：

1,2,4-triazole; DBU; regioselective alkylation; rizatriptan;

D O I：

10.1016/S0040-4039(99)02272-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The alkylation of 1,2,4-triazole with 4-nitrobenzyl halides and a variety of bases afforded the 1- and 4-alkylated isomers with a consistent regioselectivity of 90:10. Previously reported regiospecific alkylations of 1,2,4-triazole were re-examined and the quoted isomer ratios were shown to depend on the isolation procedure. The use of DBU as base in the alkylation of 1,2,4-triazole allows for a convenient and high yielding synthesis of 1-substituted-1,2,4-triazoles. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：1297 / 1301

页数：5

共 25 条

[1]

ABENHAIM D, 1994, HETEROCYCLES, V38, P793

[2]

ANDREINI F, 1989, FARMACO, V44, P831

[3] SYNTHESIS OF 1-ALKYL-1,2,4-TRIAZOLES - A NEW ONE-POT REGIOSPECIFIC PROCEDURE [J].

ASTLEFORD, BA ;

GOE, GL ;

KEAY, JG ;

SCRIVEN, EFV .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (03) :731-732

[4]

BALASUBRAMANIAN M, 1994, HETEROCYCLES, V37, P1951

[5]

BENTLEY WT, 1998, TETRAHEDRON LETT, V30, P4013

[6]

CARLSEN P, 1996, MOLECULES, V1, P242

[7] SYNTHESIS OF THE 5-HT1D RECEPTOR AGONIST MK-0462 VIA A PD-CATALYZED COUPLING REACTION [J].

CHEN, CY ;

LIEBERMAN, DR ;

LARSEN, RD ;

REAMER, RA ;

VERHOEVEN, TR ;

REIDER, PJ ;

COTTRELL, IF ;

HOUGHTON, PG .

TETRAHEDRON LETTERS, 1994, 35 (38) :6981-6984

[8] A methylene bridge as protecting group .1. Selective preparation of 4-alkyl-1,2,4-triazoles [J].

DiezBarra, E ;

delaHoz, A ;

RodriguezCuriel, RI ;

Tejeda, J .

TETRAHEDRON, 1997, 53 (06) :2253-2260

[9]

ElGhomari MJ, 1997, J PHYS ORG CHEM, V10, P669

[10]

Garratt P. J., 1996, COMPREHENSIVE HETERO, V4, P127, DOI DOI 10.1016/B978-008096518-5.00080-0

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