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Synthesis and Functionalization of 5,7‐Dinitroquinoline and Its N ‐Oxide
Author(s) -
Starosotnikov Alexey M.,
Nikol'skiy Vladislav V.,
Borodulya Anastasiya N.,
Kachala Vadim V.,
Bastrakov Maxim A.,
Solkan Vitaly N.,
Shevelev Svyatoslav A.
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201600065
Subject(s) - chemistry , sodium azide , reagent , surface modification , azide , quinoline , oxide , combinatorial chemistry , organic chemistry
An efficient method was developed for the synthesis of 5,7‐dinitroquinoline and its N ‐oxide. The reactions of these compounds with either thiols or sodium azide resulted in the regiospecific substitution of 5‐NO 2 group and the formation of previously unknown quinoline derivatives. The 5‐azido derivatives underwent reactions with 1,3‐dicarbonyl compounds and, depending on the nature of reagent, afforded either 5‐(1,2,3‐triazol)‐1‐yl‐ or 5‐amino‐7‐nitroquinolines, which have been previously inaccessible by using other methods.