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Dihydrofuran ring opening in the reactions of 2,3- dihydrofuro[3,2-c]coumarin-3-one with arylhydrazines

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Abstract

2,3-Dihydrofuro[3,2-c]coumarin-3-one reacts with arylhydrazines via two routes. The corresponding hydrazones are formed from arylhydrazines in alcohol and nitrophenylhydrazines in acetic acid or toluene. With phenylhydrazine and para-tolylhydrazine in toluene, 2,3-dihydrofuro[3,2-c]coumarin-3-one reacts unusually undergoing dihydrofuran ring opening and the formation of the corresponding 3-(2-imino-1-(2-arylhydrazinyl)ethylidene)-chromane-2,4-diones. The solvatochromic properties of the synthesized compounds were studied using electronic absorption spectra and quantum chemical calculations.

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Authors and Affiliations

  1. D. I. Mendeleev Russian University of Chemical Technology, 9 Miusskaya pl., 125047, Moscow, Russian Federation

    N. A. Kondratova, N. P. Solov’eva & V. F. Traven

Authors
  1. N. A. Kondratova
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  2. N. P. Solov’eva
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  3. V. F. Traven
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Correspondence to V. F. Traven.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1571-1578, August, 2010.

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Kondratova, N.A., Solov’eva, N.P. & Traven, V.F. Dihydrofuran ring opening in the reactions of 2,3- dihydrofuro[3,2-c]coumarin-3-one with arylhydrazines. Russ Chem Bull 59, 1612–1620 (2010). https://doi.org/10.1007/s11172-010-0285-y

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  • DOI: https://doi.org/10.1007/s11172-010-0285-y

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