β-Cyclodextrin-mediated highly efficient [2+3] cycloaddition reactions for the synthesis of 5-substituted 1H-tetrazoles

被引：64

作者：

Patil, Dipak R. ^{[1
]}

Wagh, Yogesh B. ^{[1
]}

Ingole, Pravin G. ^{[2
]}

Singh, Kripal ^{[2
]}

Dalal, Dipak S. ^{[1
]}

机构：

[1] North Maharashtra Univ, Sch Chem Sci, Dept Organ Chem, Jalgaon 425001, MS, India

[2] Council Sci & Ind Res CSIR, Cent Salt & Marine Chem Res Inst, Bhavnagar 364021, Gujarat, India

来源：

NEW JOURNAL OF CHEMISTRY | 2013年 / 37卷 / 10期

关键词：

CATALYZED SYNTHESIS; RECEPTOR ANTAGONISTS; TETRAZOLE FORMATION; REUSABLE CATALYST; NITRILES; AZIDE; COMPLEXES; ACID; N; N-DIMETHYLFORMAMIDE; CHEMISTRY;

D O I：

10.1039/c3nj00569k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A beta-cyclodextrin-promoted [2+3] cycloaddition reaction between nitriles and sodium azide in the presence of ammonium chloride in DMF at 120 degrees C is reported, affording various 5-substituted 1H-tetrazoles in good to excellent yields in short reaction times. The presence of beta-CD renders the formation of a precipitate-like gel in the reaction media when heated. No precipitation occurs in the absence of NaN3 and NH4Cl. The precipitation responses with other salts such as LiCl and NiCl2 were weaker than with NH4Cl. In the present paper the application of supramolecular aggregates is reported for the [2+3] cycloaddition reaction. beta-Cyclodextrin can be recovered and reused without any significant loss of activity.

引用

页码：3261 / 3266

页数：6

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