Nucleophilic dearomatization of 4-aza-6-nitrobenzofuroxan by CH acids in the synthesis of pharmacology-oriented compounds

Nucleophilic dearomatization of 4-aza-6-nitrobenzofuroxan by CH acids in the synthesis of pharmacology-oriented compounds Full article

Journal

Beilstein Journal of Organic Chemistry
ISSN: 2195-951X , E-ISSN: 1860-5397

Output data

Year: 2017, Volume: 13, Pages: 2854-2861 Pages count : 8 DOI: 10.3762/bjoc.13.277

Authors

Starosotnikov Alexey M ¹ , Shkaev Dmitry V ¹ , Bastrakov Maxim A ¹ , Fedyanin Ivan V ² , Shevelev Svyatoslav A ¹ , Dalinger Igor L ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Leninsky prosp. 47, Moscow 119991, Russia and
2	A.N. Nesmeyanov Institute of Organoelement Compounds, Vavilova str. 28, Moscow 119991, Russia

4-Aza-6-nitrobenzofuroxan (ANBF) reacts with 1,3-dicarbonyl compounds and other CH acids to give carbon-bonded 1,4-adducts – 1,4-dihydropyridines fused with furoxan ring. In the case of most acidic β-diketones, which exist mainly in the enol form in polar solvents, the reactions proceed in the absence of any added base emphasizing the highly electrophilic character of ANBF. The resulting compounds combine in one molecule NO-donor furoxan ring along with a pharmacologically important 1,4-dihydropyridine fragment and therefore can be considered as prospective platforms for the design of pharmacology-oriented heterocyclic systems.

Starosotnikov A.M. , Shkaev D.V. , Bastrakov M.A. , Fedyanin I.V. , Shevelev S.A. , Dalinger I.L.
Nucleophilic dearomatization of 4-aza-6-nitrobenzofuroxan by CH acids in the synthesis of pharmacology-oriented compounds
Beilstein Journal of Organic Chemistry. 2017. V.13. P.2854-2861. DOI: 10.3762/bjoc.13.277 WOS Scopus OpenAlex

Web of science:	WOS:000423178000002
Scopus:	2-s2.0-85040443995
OpenAlex:	W2776313750

DB	Citing
OpenAlex	19
Scopus	20
Web of science	19