Novel chemical modifications at the 4-position of chromones. Synthesis and reactivity of 4H-chromene-4-spiro-5 `-isoxazolines and related compounds / Sosnovskikh VY,Usachev BI,Sizov AY,Kodess MI // TETRAHEDRON LETTERS. - 2004. - V. 45, l. 39. - P. 7351-7354.

ISSN/EISSN:

0040-4039 / нет данных

Type:

Article

Abstract:

Reactions of chromones with dilithiooximes proceed via nucleophilic 1,2-addition to give, on acidification, 4H-chromene-4-spiro-5'-isoxazoline derivatives in high yields. On treatment with concentrated H2SO4 the isoxazoline ring of this novel spiroannulated heterocyclic system opens to give alpha,beta-unsaturated oximes, which undergo nitrosation, bromination, and the Beckmann rearrangement to the corresponding spiroisoxazolines and alpha, beta-unsaturated amides, respectively. The latter can be obtained directly by the Beckmann rearrangement of 4H-chromene-4-spiro-5'-isoxazolines. (C) 2004 Elsevier Ltd. All rights reserved.

Author keywords:

chromones; dilithiooximes; 4H-chromene-4-spiro-5 `-isoxazolines; alpha,beta-unsaturated oximes; Beckmann rearrangement; nitrosation; bromination REGIOSPECIFIC SYNTHESIS; 3-SUBSTITUTED 5-ALKYLISOXAZOLES; ALPHA,BETA-UNSATURATED OXIMES; DILITHIATED C(ALPHA),O-OXIMES; ANTIANAPHYLACTIC AGENTS; ANTIALLERGIC SUBSTANCES; ISOXAZOLES; DERIVATIVES; 1,4-TRIFLUOROMETHYLATION; NITROSATION

DOI:

10.1016/j.tetlet.2004.07.158

Web of Science ID:

ISI:000224017200041

Соавторы в МНС:

Другие поля

Поле	Значение
Month	SEP 20
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	REGIOSPECIFIC SYNTHESIS; 3-SUBSTITUTED 5-ALKYLISOXAZOLES; ALPHA,BETA-UNSATURATED OXIMES; DILITHIATED C(ALPHA),O-OXIMES; ANTIANAPHYLACTIC AGENTS; ANTIALLERGIC SUBSTANCES; ISOXAZOLES; DERIVATIVES; 1,4-TRIFLUOROMETHYLATION; NITROSATION
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	vyacheslav.sosnovskikh@usu.ru
Number-of-Cited-References	32
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	7
Journal-ISO	Tetrahedron Lett.
Doc-Delivery-Number	856AY