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金属三氟甲磺酸盐催化的烯烃、N-溴代丁二酰亚胺、腈和三甲基硅基叠氮化物的反应：1,5-二取代四唑的合成

Metal triflate catalyzed reactions of alkenes, NBS, nitriles, and TMSN3: synthesis of 1,5-disubstituted tetrazoles.

作者信息

Hajra Saumen, Sinha Debarshi, Bhowmick Manishabrata

机构信息

Department of Chemistry, Indian Institute of Technology, Kharagpur 721 302, India.

出版信息

J Org Chem. 2007 Mar 2;72(5):1852-5. doi: 10.1021/jo062432j. Epub 2007 Feb 1.

DOI:10.1021/jo062432j

PMID:17266377

Abstract

A versatile and highly efficient protocol for the synthesis of 1,5-disubstituted tetrazoles has been developed by metal triflate catalyzed one-pot reaction of alkenes, NBS, nitriles, and TMSN3. Among the metal triflates, Zn(OTf)2 was found to be the best catalyst. Use of different combinations of alkenes and nitriles generate a variety of 1,5-disubstituted tetrazoles containing an additional alpha-bromo functionality of the N1-alkyl substituent.

摘要

通过金属三氟甲磺酸盐催化的烯烃、N-溴代丁二酰亚胺（NBS）、腈和三甲基硅基叠氮化物（TMSN3）的一锅反应，开发了一种通用且高效的合成1,5-二取代四唑的方法。在金属三氟甲磺酸盐中，发现Zn(OTf)2是最佳催化剂。使用不同组合的烯烃和腈可生成多种含有N1-烷基取代基额外α-溴官能团的1,5-二取代四唑。