Acid Catalyzed tert-Butylation and Tritylation of 4-Nitro-1,2,3-triazole: Selective Synthesis of 1-Methyl-5-nitro-1,2,3-triazole via 1-tert-Butyl-4-nitro-1,2,3-triazole

被引：10

作者：

Filippova, Yuliya V. ^{[2
]}

Sukhanova, Anna G. ^{[2
]}

Voitekhovich, Sergei V. ^{[1
]}

Matulis, Vadim E. ^{[1
]}

Sukhanov, Gennady T. ^{[2
]}

Grigoriev, Yury V. ^{[1
]}

Ivashkevich, Oleg A. ^{[1
]}

机构：

[1] Belarusian State Univ, Res Inst Physicochem Problems, Minsk 220030, BELARUS

[2] Russian Acad Sci, Inst Problems Chem & Energet Technol, Siberian Branch, Biisk 659322, Russia

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2012年 / 49卷 / 04期

关键词：

5-SUBSTITUTED TETRAZOLES; REGIOSELECTIVE SYNTHESIS; N-ALKYLATION;

D O I：

10.1002/jhet.933

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

4-Nitro-1,2,3-triazole was found to react with tert-butanol in concentrated sulfuric acid to yield 1-tert-butyl-4-nitro-1,2,3-triazole as the only reaction product, whereas tert-butylation and tritylation of 4-nitro-1,2,3-triazole in presence of catalytic amount of sulfuric acid in benzene was found to provide mixtures of isomeric 1- and 2-alkyl-4-nitro-1,2,3-triazoles with predominance of N2-alkylated products. A new methodology for preparation of 1-alkyl-5-nitro-1,2,3-triazoles from 1-tert-butyl-4-nitro-1,2,3-triazole via exhaustive alkylation followed by removal of tert-butyl group from intermediate triazolium salts was demonstrated by the example of preparation of 1-methyl-5-nitro-1,2,3-triazole.

引用

页码：965 / 968

页数：4

共 50 条

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