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

Autor:	Sergey I. Filimonov, Galina A. Stashina, Kyrill Yu. Suponitsky, Igor G. Abramov, Dmitriy V. Khakimov, Yuri A. Strelenko, Tatyana S. Pivina, Sergey I. Firgang, Zhanna V. Chirkova, Alexander V. Samet
Rok vydání:	2012
Předmět:	chemistry.chemical_classification Base (chemistry) Stereochemistry Organic Chemistry Biochemistry chemistry.chemical_compound chemistry Group (periodic table) Yield (chemistry) Intramolecular force Drug Discovery Nitro Displacement (orthopedic surgery) Nitrite Alkyl
Zdroj:	Tetrahedron. 68:5991-5997
ISSN:	0040-4020
DOI:	10.1016/j.tet.2012.05.034
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::cd900b7fc3c2d3f12af1aaa1cf543c31 https://doi.org/10.1016/j.tet.2012.05.034 Zobrazit plný text záznamu Full Text from ScienceDirect