Modifications of 7-hydroxy- 3-(benzothiazol-2-yl)coumarin

Authors

DOI:

https://doi.org/10.15407/dopovidi2021.05.090

Keywords:

7-hydroxy-3-benzothiazolylcoumarin, aminomethylation, formylation, homoisoflavones, recyclization

Abstract

This paper is devoted to 7-hydroxy-3-(benzothiazol-2-yl)coumarin modifications using the dimethylaminomethyl and formyl groups introduced in 8 position, useful for further structural transformations. Derivatives of the dihydrooxazinocoumarin system were obtained by aminomethylation of 7-hydroxy-3-(benzothiazol-2-yl) coumarin under the classical Mannich reaction conditions using an excess of formalin. Starting from 8-dialkylaminomethyl-7-hydroxy-3-(benzothiazol-2-yl)coumarin the corresponding Mannich bases were synthesized by transamination with benzylamines, homoisoflavone derivatives were obtained as a result of the interaction with o-hydroxyarene enaminoketones and 3-(benzothiazol-2-yl)-7-hydroxy-8-formylcoumarin was obtained under the Duff reaction conditions. The latter in the reaction with 4-nitrophenacyl bromide formed the furo[2,3-h]coumarin system derivative. The recyclizations of 3-(benzothiazol-2-yl)-7-hydroxy- 8-(4-oxo-4H-3-chromenylmethyl)-2H-2-chromenone under the action of binucleophiles were studied.

References

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Published

27.10.2021

How to Cite

Shokol Т., Suprun А., Hlibov Є., Moskvina В., & Khilya В. (2021). Modifications of 7-hydroxy- 3-(benzothiazol-2-yl)coumarin. Reports of the National Academy of Sciences of Ukraine, (5), 90–98. https://doi.org/10.15407/dopovidi2021.05.090