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Thioamide derivatives of cannabinoids. A study of the influence of the thioamide function on regiochemistry in the synthesis of thioamide cannabinoids from 2,4‐dihydroxybenzothioamides
Author(s) -
Sośnicki Jacek,
Jagodziński Tadeusz,
Królikowska Miroslawa
Publication year - 1999
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570360434
Subject(s) - thioamide , chemistry , regioselectivity , nitromethane , citronellal , resorcinol , boron trifluoride , organic chemistry , acetic acid , medicinal chemistry , catalysis
Several thiocarbamoyl derivatives of cannabinoids were obtained in the collidine‐catalysed condensation of 2,4‐dihydroxybenzothioamides with citral and citronellal. The thioamide function was found to change the regioselective preferences of the reaction as compared with the known cannabinoid syntheses from hydroxyacetophenones. The experimental results and theoretical (FMO theory) considerations made it possible to advance the reaction mechanism. Convenient methods were developed for the synthesis of the starting 2,4‐dihydroxybenzothioamides from resorcinol and isothiocyanates in the presence of the boron trifluoride/acetic acid 1:2 complex or aluminum chloride in nitromethane.