Reactions of 3-(polyfluoroacyl)chromones with hydroxylamine. The first synthesis of 3-cyano-2-(polyfluoroalkyl)chromones / Sosnovskikh Vyacheslav Ya.,Moshkin Vladimir S.,Irgashev Roman A. // TETRAHEDRON LETTERS. - 2006. - V. 47, l. 48. - P. 8543-8546.

ISSN/EISSN:

0040-4039 / нет данных

Type:

Article

Abstract:

Reaction of 3-(polyfluoroacyl)chromones with hydroxylamine proceeds via nucleophilic 1,4-addition followed by opening of the pyrone ring and subsequent cyclization to 4-(polyfluoroalkyl)-4H-chromeno{[}3,4-d]isoxazol-4-ols in good yields. On treatment with trifluoroacetic acid, the isoxazole ring of this annulated heterocyclic system opens to give 3-eyano-2-(polyfluoroalkyl)chromones. Reaction F of 3-(polyfluoi-oacyl)chromones with hydroxylamine hydrochloride occurs only at the carbonyl carbon atom connected to the R group to give the corresponding oximes in low yields. (c) 2006 Elsevier Ltd. All rights reserved.

Author keywords:

3-(polyfluoroacyl)chromones; hydroxylamine; 4H-chromeno{[}3,4-d]isoxazol-4-ols; 3-cyano-2-(polyfluoroalkyl)chromones; oximes 1,3-BIS-SILYL ENOL ETHERS; BENZO-GAMMA-PYRONES; ANTIANAPHYLACTIC AGENTS; CONVENIENT SYNTHESIS; CONJUGATE ADDITION; VERSATILE SYNTHON; CHROMONES; 3-FORMYLCHROMONE; DERIVATIVES; 3-ACYLCHROMONES

DOI:

10.1016/j.tetlet.2006.09.136

Web of Science ID:

ISI:000242137400022

Соавторы в МНС:

Другие поля

Поле	Значение
Month	NOV 27
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	1,3-BIS-SILYL ENOL ETHERS; BENZO-GAMMA-PYRONES; ANTIANAPHYLACTIC AGENTS; CONVENIENT SYNTHESIS; CONJUGATE ADDITION; VERSATILE SYNTHON; CHROMONES; 3-FORMYLCHROMONE; DERIVATIVES; 3-ACYLCHROMONES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	Vyacheslav.Sosnovskikh@usu.ru
ResearcherID-Numbers	Moshkin, Vladimir/E-6623-2017 Irgashev, Roman/E-5077-2017
ORCID-Numbers	Irgashev, Roman/0000-0002-8428-1748
Number-of-Cited-References	53
Usage-Count-Since-2013	6
Journal-ISO	Tetrahedron Lett.
Doc-Delivery-Number	106YH