Facile Dearomatization of Nitroquinolines through [3+2] and [4+2] Cycloaddition Reactions

Facile Dearomatization of Nitroquinolines through [3+2] and [4+2] Cycloaddition Reactions Full article

Journal

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

Output data

Year: 2015, Volume: 4, Number: 2, Pages: 146-153 Pages count : 8 DOI: 10.1002/ajoc.201402207

Authors

Bastrakov Maxim A. ¹ , Starosotnikov Alexey M. ¹ , Kachala Vadim V. ¹ , Fedyanin Ivan V. ² , Shevelev Svyatoslav A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, Moscow 119991 (Russia)
2	Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova st., Moscow 119991 (Russia)

An efficient method was developed for the functionalization of nitroquinolines by employing pericyclic [3+2] and [4+2] cycloaddition reactions. The facile dearomatization of the nitrated benzene ring under the action of unstabilized N-alkyl azomethine ylides and dienes led to fused heterocyclic systems. The 1,3-dipoles smoothly and selectively underwent a cycloaddition reaction with the CC(NO2) fragment of the aromatic system if the position ortho to the nitro group was vacant, whereas the [4+2] cycloaddition of dienes required a furoxan ring to be annulated to the quinoline moiety.

Bastrakov M.A. , Starosotnikov A.M. , Kachala V.V. , Fedyanin I.V. , Shevelev S.A.
Facile Dearomatization of Nitroquinolines through [3+2] and [4+2] Cycloaddition Reactions
Asian Journal of Organic Chemistry. 2015. V.4. N2. P.146-153. DOI: 10.1002/ajoc.201402207 WOS Scopus OpenAlex

Web of science:	WOS:000349147900008
Scopus:	2-s2.0-84922058903
OpenAlex:	W1603023661

DB	Citing
OpenAlex	29
Scopus	29
Web of science	28