Metal-Catalyzed Isomerization of 5-Heteroatom-Substituted Isoxazoles as a New Route to 2-Halo-2H-azirines

Nikolai V. Rostovskii, Anastasiya V. Agafonova, Ilia A. Smetanin, Mikhail S. Novikov*, Alexander F. Khlebnikov, Julia O. Ruvinskaya, Galina L. Starova

*Saint Petersburg State University, Institute of Chemistry, 7/9 Universitetskaya nab., St. Petersburg, 199034, Russian Federation, Email: m.novikovspbu.ru

N. V. Rostovskii, A. V. Agafonova, I. A. Smetanin, M. S. Novikov, A. F. Khlebnikov, J. O. Ruvinskaya, G. L. Starova, Synthesis, 2017, 49, 4478-4488.

DOI: 10.1055/s-0036-1590822

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Abstract

Rh₂(Piv)₄ catalyzes a convenient gram-scale method for the preparation of 2-halo-2H-azirine-2-carboxylic acid esters and amides from 5-heteroatom-substituted 4-haloisoxazoles. In addition, rhodium catalysis is successfully applied in the synthesis of azirine-2-carboxylates from non-halogenated 5-alkoxyisoxazoles.

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Key Words

azirines, isoxazoles, haloheterocycles, rhodium(II) carboxylates, iron(II) chloride, catalysis, isomerization

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ID: J66-Y2017