Synthesis of 5-Substituted 1H-Tetrazoles from Nitriles by Continuous Flow: Application to the Synthesis of Valsartan

被引：23

作者：

Carpentier, Florian ^{[1
]}

Felpin, Francois-Xavier ^{[1
]}

Zammattio, Francoise ^{[1
]}

Le Grognec, Erwan ^{[1
]}

机构：

[1] Univ Nantes, CNRS, CEISAM, UMR 6230, F-44000 Nantes, France

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2020年 / 24卷 / 05期

关键词：

continuous flow; tetrazole; organotin; azide; polymer-supported reagent; CATALYZED SYNTHESIS; HYDRAZOIC ACID; CHEMISTRY; TETRAZOLES; REAGENTS; SAFE; CYCLOADDITION; SALTS;

D O I：

10.1021/acs.oprd.9b00526

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An efficient continuous flow process for the synthesis of 5-substituted 1H-tetrazoles is described. The process involves the reaction between a polymer-supported triorganotin azide and organic nitriles. The polymer-supported organotin azide, which is in situ generated with a polystyrene-supported triorganotin alkoxide and trimethylsilylazide, is immobilized in a packed bed reactor. This approach is simple, fast (it takes from 7.5 to 15 min), and guarantees a low concentration of tin residues in the products (<5 ppm). The process was developed to aryl-, heteroaryl-, and also alkylnitriles and was applied for the synthesis of valsartan, an angiotensin II receptor antagonist.

引用

页码：752 / 761

页数：10

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