AN AgOAc-CATALYZED REACTION OF 3-NITRO-2<i>H</i>-CHROMENES WITH ETHYL DIAZOACETATE: AN EFFICIENT ONE-POT SYNTHESIS OF ETHYL 3,4-DIHYDROCHROMENO[3,4-<i>c</i>]PYRAZOLE-1-CARBOXYLATES

Authors

  • Людмила С. Быкова Institute of Natural Sciences and Mathematics of the Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 Lenin Ave., Yekaterinburg 620000
  • Иван А. Кочнев Institute of Natural Sciences and Mathematics of the Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 Lenin Ave., Yekaterinburg 620000
  • Алексей Ю. Барков Institute of Natural Sciences and Mathematics of the Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 Lenin Ave., Yekaterinburg 620000
  • Николай С. Зимницкий Institute of Natural Sciences and Mathematics of the Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 Lenin Ave., Yekaterinburg 620000
  • Владислав Ю. Коротаев Institute of Natural Sciences and Mathematics of the Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 Lenin Ave., Yekaterinburg 620000
  • Вячеслав Я. Сосновских Institute of Natural Sciences and Mathematics of the Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 Lenin Ave., Yekaterinburg 620000

DOI:

https://doi.org/10.1007/7001

Keywords:

chromeno[3, 4-c]pyrazoles, ethyl diazoacetate, 3-nitro-2H-chromenes, 1, 3-dipolar cycloaddition

Abstract

A regioselective method for the synthesis of ethyl 3,4-dihydrochromeno[3,4-c]pyrazole-1-carboxylates from 2-substituted 3-nitro-2H-chromenes and ethyl diazoacetate in 68–87% yields was developed. This approach involves an AgOAc-catalyzed 1,3-dipolar cycloaddition of ethyl diazoacetate to nitrochromenes followed by elimination of HNO2 by the action of DBU.

Authors: Lyudmila S. Bykova, Ivan А. Kochnev*, Alexey Yu. Barkov, Nikolay S. Zimnitskiy, Vladislav Yu. Korotaev*, Vyacheslav Ya. Sosnovskikh

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Published

2022-11-17

Issue

Vol. 58 No. 11 (2022)

Section

Original Papers