Open AccessRearrangement of spiroderivatives of 1,3-benzo(naphtho)dioxin-4(1)-ones as a new method of synthesis of xanthene bromo derivatives
Author(s) -
Anton V. Kovtun,
Светлана А. Варениченко,
Ekaterina V. Zaliznaya,
А. В. Мазепа,
Oleg К. Farat,
В. И. Марков
Publication year - 2021
Publication title -
voprosy himii i himičeskoj tehnologii/voprosy himii i himičeskoj tehnologii
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.278
H-Index - 7
eISSN - 2413-7987
pISSN - 0321-4095
DOI - 10.32434/0321-4095-2021-137-4-73-77
Subject(s) - xanthene , chemistry , reagent , bromine , hydrolysis , organic chemistry , perchlorate , medicinal chemistry , ion
We have proposed a method for the synthesis of previously unknown bromo xanthenes using the reagent PBr3/DMF as a rearrangement initiator. Bromo derivatives of xanthenes in the form of organic perchlorates were prepared by reacting the corresponding benzo(naphtho)dioxin-4(1)-ones with a three-fold excess of Vilsmeier-Haack PBr3/DMF reagent at 1100C for 2 hours, followed by the addition of sodium perchlorate. The conditions for the synthesis of formyl derivatives of xanthenes under conditions of acid hydrolysis were selected. The structure of the compounds was confirmed by 1H and 13C NMR spectral data and mass spectrometry. Preliminary studies showed that it is possible to selectively replace the dimethylamino group and the bromine atom with various nucleophiles in bromo derivatives of xanthenes, which opens up wide possibilities for the synthesis of low-molecular building blocks and dyes.