Synthesis and reactivity of 4-hydroxy-5-methyl-2-(2-oxo-2H-chromen-3-yl)-6H-1,3-oxazin-6-ones


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Abstract

4-Hydroxy-6H-1,3-oxazin-6-ones with a coumarin fragment in position 2 of the oxazine ring were synthesized. Their hydrolysis, alcoholysis, and hydrazinolysis afforded a number of new coumarin derivatives containing malonamic acid and 1,2,4-triazole residues. The low stability of the title compounds toward oxygencentered nucleophiles was interpreted by quantum chemical calculations.

About the authors

N. M. Chernov

St. Petersburg State Chemical Pharmaceutical Academy

Author for correspondence.
Email: nikita.chernov@pharminnotech.com
Russian Federation, ul. Professora Popova 14/A, St. Petersburg, 197376

P. V. Filippova

St. Petersburg State Chemical Pharmaceutical Academy

Email: nikita.chernov@pharminnotech.com
Russian Federation, ul. Professora Popova 14/A, St. Petersburg, 197376

I. P. Yakovlev

St. Petersburg State Chemical Pharmaceutical Academy

Email: nikita.chernov@pharminnotech.com
Russian Federation, ul. Professora Popova 14/A, St. Petersburg, 197376

V. E. Zakhs

St. Petersburg State Chemical Pharmaceutical Academy

Email: nikita.chernov@pharminnotech.com
Russian Federation, ul. Professora Popova 14/A, St. Petersburg, 197376

A. V. Belyakov

St. Petersburg State Institute of Technology (Technical University)

Email: nikita.chernov@pharminnotech.com
Russian Federation, Moskovskii pr. 26, St. Petersburg, 190013


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