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Oxidative Dearomatization as a Strategy for a Facile, Metal‐Free Synthesis of Vanillyl Benzodiazepines
Author(s) -
Nunewar Saiprasad N.,
Sangu Komal G.,
Kotla Naveen K.,
Tangellamudi Neelima D.
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202002523
Subject(s) - chemistry , moiety , organic chemistry , oxidative phosphorylation , methylene , combinatorial chemistry , biochemistry
Abstract isovanillin was conveniently dearomatized into synthetically useful o ‐quinol acetate by treatment with phenyliodine(III) diacetate (PIDA) in methylene chloride at low temperature. Subsequent treatment with o ‐aryl diamines directly furnished vanillyl benzodiazepines in good yields. Vanillyl benzodiazepines, could be the prospective objects of investigation in medicinal chemistry considering the central nervous system depressant activity of benzodiazepines and potent antioxidant and anti‐inflammatory activities of vanillyl moiety by being present in a single framework. Herein we propose a simple, metal‐free, and efficient approach for the synthesis of vanillyl benzodiazepines via oxidative dearomatization. The regio‐chemistry of product isomers were established by NOE studies.