From N-substituted thioamides to symmetrical and unsymmetrical 3,4,5-trisubstituted 4H-1,2,4-triazoles:: Synthesis and characterisation of new chelating ligands

被引：116
|
作者：
Klingele, MH [1 ]
Brooker, S [1 ]
机构：
[1] Univ Otago, Dept Chem, Dunedin, New Zealand
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 2004卷 / 16期
关键词：
1,2,4-triazoles; thioamides; N ligands; NMR spectroscopy; X-ray diffraction;
D O I：
10.1002/ejoc.200400184
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An improved protocol for the synthesis of N-substituted pyridine-2-thiocarboxamides under the conditions of the Willgerodt-Kindler reaction, employing a catalytic amount of sodium sulfide nonahydrate, has been developed. Following this protocol, eight thioamides carrying aromatic or aliphatic N-substituents have been prepared in good to excellent yields. Condensation of these thioamides or their S-alkylated congeners with hydrazides in refluxing 1-butanol has afforded eight unfused 3,4,5-trisubstituted 4H-1,2,4-triazoles in good yields, including four examples of the otherwise not easily obtainable 4-alkyl-3,5-diaryl-4H-1,2,4-triazoles. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
引用
收藏
页码：3422 / 3434
页数：13
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