CERTAIN CASES OF o-ALKOXYCINNAMIC ACIDS CREATION FROM COUMARINS IN O-ALKYLATION CONDITION

DOI: https://doi.org/10.17721/1728-2209.2019.1(56).6

Authors

  • S. Shilin Taras Shevchenko National University of Kyiv image/svg+xml
  • O. Shablykina Taras Shevchenko National University of Kyiv image/svg+xml
  • O. Shablykin The V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine
  • V. Khilya Taras Shevchenko National University of Kyiv image/svg+xml
  • Z. Nagorna Taras Shevchenko National University of Kyiv image/svg+xml

Keywords:

coumarin, O-alkylation, o-alkoxycinnamic acid

Abstract

The experiments showed that the 3-azolylcoumarins and furo[3,2-g]coumarins coumarin cycle's opening occurs only in aqueous alkali, and when alkylated in an organic solvent in the presence of K2CO3, the lactone fragment remains unchanged. The 7-hydroxy-6-(isocoumarin-3-yl)-4-methylcoumarin cycle turned out to be more labile. The result of alkylation of this compound with ethyl acetate of chloroacetic acid in the presence of K2CO3 depended on the nature of the aprotic solvent and the temperature of reaction. So, when this reaction was carried out in boiling acetone, only the free hydroxyl group at position 7 of coumarin was alkylated. But when the initial coumarin was heated at 100 °С with an excess of an alkylating agent in DMSO, simultaneous alkylation of both the free 7-OH group and the endocyclic Oxygen atom occurred.

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Published

2019-12-04

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Vol. 56 No. 1 (2019): Bulletin Taras Shevchenko National University of Kyiv. Chemistry

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Copyright (c) 2019 С. Шилін, О. Шабликіна, О. Шабликін, В. Хиля, З. Нагорна

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How to Cite

CERTAIN CASES OF o-ALKOXYCINNAMIC ACIDS CREATION FROM COUMARINS IN O-ALKYLATION CONDITION: DOI: https://doi.org/10.17721/1728-2209.2019.1(56).6. (2019). Bulletin of the Taras Shevchenko National University of Kyiv. Chemistry, 56(1), 25-30. https://chemistry.bulletin.knu.ua/article/view/8362

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