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Synthesis of a New Family of 1,1-Diazidoethenes: One-Pot Construction of 4-Azido-1,2,3-triazoles via Nitrene Cyclization

Alexey V. Shastin, Biligma D. Tsyrenova, Pavel G. Sergeev, Vitaly A. Roznyatovsky, Ivan V. Smolyar, Victor N. Khrustalev, Valentine G. Nenajdenko*

*Department of Chemistry, Lomonosov Moscow State University, 119899 Moscow, Russia, Email: nenajdenkoorg.chem.msu.ru

A. V. Shastin, B. T. Tsyrenova, P. G. Sergeev, V. A. Roznyatovsky, I. V. Smolyar, V. N. Khrustalev, V. G. Nenajdenko, Org. Lett., 2018, 20, 7803-7806.

DOI: 10.1021/acs.orglett.8b03227 (free Supporting Information)



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Abstract

The reaction of 4,4-dichloro-1,2-diazabuta-1,3-dienes with sodium azide provides extremely rare 1,1-bisazides. These highly unstable compounds are prone to eliminate N2 to cyclize into 4-azido-1,2,3-triazoles bearing two aryl groups at positions 2 and 5. This reaction enables a highly efficient synthesis of various 4-azidotriazoles. These heterocycles are highly attractive building blocks.

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Key Words

1,2,3-triazoles


ID: J54-Y2018