Base-induced transformations of ortho-nitrobenzylketones: intramolecular displacement of nitro group versus nitro-nitrite rearrangement

Base-induced transformations of ortho-nitrobenzylketones: intramolecular displacement of nitro group versus nitro-nitrite rearrangement Full article

Journal

Tetrahedron
ISSN: 0040-4020 , E-ISSN: 1464-5416

Output data

Year: 2012, Volume: 68, Number: 30, Pages: 5991-5997 Pages count : 7 DOI: 10.1016/j.tet.2012.05.034

Authors

Filimonov Sergey I. ¹ , Chirkova Zhanna V. ¹ , Abramov Igor G. ¹ , Firgang Sergey I. ² , Stashina Galina A. ² , Strelenko Yuri A. ² , Khakimov Dmitriy V. ² , Pivina Tatyana S. ² , Samet Alexander V. ² , Suponitsky Kyrill Yu. ³

Affiliations

1	Yaroslavl State Technical University, 88 Moskovsky Pr, 150023 Yaroslavl, Russian Federation
2	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Pr., 119991 Moscow, Russia
3	A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov St., 119991 Moscow, Russia

Reactions of 4-bromo-5-nitrophthalonitrile (BNPN) with enolates of alkyl 4-R-2,4-dioxobutanoates gave alkyl 3-acyl-5,6-dicyanobenzofuran-2-carboxylates, 4-(2-R-2-oxoethyl)-5-nitrophthalonitriles, or 3-acyl-1,2-benzoxazole-5,6-dicarbonitriles. With a base, 4-(2-R-2-oxoethyl)-5-nitrophthalonitriles either undergo nitro-nitrite rearrangement resulting in 3-acyl-1,2-benzoxazole-5,6-dicarbonitriles or yield 2-R-benzofuran-5,6-dicarbonitriles with a nitro group displacement.

Filimonov S.I. , Chirkova Z.V. , Abramov I.G. , Firgang S.I. , Stashina G.A. , Strelenko Y.A. , Khakimov D.V. , Pivina T.S. , Samet A.V. , Suponitsky K.Y.
Base-induced transformations of ortho-nitrobenzylketones: intramolecular displacement of nitro group versus nitro-nitrite rearrangement
Tetrahedron. 2012. V.68. N30. P.5991-5997. DOI: 10.1016/j.tet.2012.05.034 WOS Scopus OpenAlex

Web of science:	WOS:000306042000005
Scopus:	2-s2.0-84862212795
OpenAlex:	W2029198310

DB	Citing
OpenAlex	23
Scopus	25
Web of science	25