Synthesis and Functionalization of 5,7‐Dinitroquinoline and Its N‐Oxide

Synthesis and Functionalization of 5,7‐Dinitroquinoline and Its N‐Oxide Full article

Journal

Asian Journal of Organic Chemistry
ISSN: 2193-5815 , E-ISSN: 2193-5807

Output data

Year: 2016, Volume: 5, Number: 5, Pages: 685-690 Pages count : 6 DOI: 10.1002/ajoc.201600065

Authors

Starosotnikov Alexey M. ¹ , Nikol'skiy Vladislav V. ¹ , Borodulya Anastasiya N. ¹ , Kachala Vadim V. ¹ , Bastrakov Maxim A. ¹ , Solkan Vitaly N. ¹ , Shevelev Svyatoslav A. ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry RAS, Leninsky prosp. 47, Moscow, 119991 Russia

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-NO2 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.

Starosotnikov A.M. , Nikol'skiy V.V. , Borodulya A.N. , Kachala V.V. , Bastrakov M.A. , Solkan V.N. , Shevelev S.A.
Synthesis and Functionalization of 5,7‐Dinitroquinoline and Its N‐Oxide
Asian Journal of Organic Chemistry. 2016. V.5. N5. P.685-690. DOI: 10.1002/ajoc.201600065 WOS Scopus OpenAlex

Web of science:	WOS:000380259700013
Scopus:	2-s2.0-84961689605
OpenAlex:	W2280691641

DB	Citing
OpenAlex	13
Scopus	11
Web of science	12