An Improved Protocol for the Preparation of 5-Substituted Tetrazoles from Organic Thiocyanates and Nitriles

Svetlana Vorona; Tatiana Artamonova; Yuri Zevatskii; Leonid Myznikov

doi:10.1055/s-0033-1340616

Synthesis, Inhaltsverzeichnis

Synthesis 2014; 46(06): 781-786
DOI: 10.1055/s-0033-1340616

paper

An Improved Protocol for the Preparation of 5-Substituted Tetrazoles from Organic Thiocyanates and Nitriles

Svetlana Vorona

Saint Petersburg State University of Technology and Design, ul. Bolshaya Morskaya 18, 191186 Saint Petersburg, Russian Federation Fax: +7(812)5719584 eMail: Myznikov_lv@mail.ru

,

Tatiana Artamonova

Saint Petersburg State University of Technology and Design, ul. Bolshaya Morskaya 18, 191186 Saint Petersburg, Russian Federation Fax: +7(812)5719584 eMail: Myznikov_lv@mail.ru

,

Yuri Zevatskii

Saint Petersburg State University of Technology and Design, ul. Bolshaya Morskaya 18, 191186 Saint Petersburg, Russian Federation Fax: +7(812)5719584 eMail: Myznikov_lv@mail.ru

,

Leonid Myznikov*

Saint Petersburg State University of Technology and Design, ul. Bolshaya Morskaya 18, 191186 Saint Petersburg, Russian Federation Fax: +7(812)5719584 eMail: Myznikov_lv@mail.ru

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Abstract

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Abstract

Organic thiocyanates and nitriles are converted efficiently into the corresponding 5-substituted 1H-tetrazoles by treatment with zinc(II) chloride and sodium azide in aliphatic alcohols. The presented procedure provides mild reaction conditions, short reaction times, and good to excellent yields for a wide range of substrates, including deactivated aliphatic nitriles and thermally unstable thiocyanates.

Key words

tetrazoles - nitriles - thiocyanates - cycloaddition - azides - zinc salts

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Referenzen

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