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Synthesis of Pyrido[2, 3‐a]phenoxazines and Pyrido[2, 3‐a]phenothiazines via Successive S N Ar Processes
Author(s) -
Starosotnikov Alexey M.,
Nikol'skiy Vladislav V.,
Bastrakov Maxim A.,
Kachala Vadim V.,
Pavlov Alexander A.,
Ugrak Bogdan I.,
Shevelev Svyatoslav A.
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201702806
Subject(s) - nitro , chlorine atom , combinatorial chemistry , base (topology) , chemistry , smiles rearrangement , medicinal chemistry , mathematics , organic chemistry , mathematical analysis , alkyl
An efficient method was developed for the synthesis of novel pyrido[2, 3‐a]phenoxazines and phenothiazines. The base‐promoted reaction of 8‐chloro‐5,7‐dinitroquinoline with binucleophiles (o‐aminophenols and o‐aminothiophenols) results in substitution of the chlorine atom followed by replacement of the nitro group. In case of aminothiophenols the products of in situ Smiles rearrangement were isolated.