Spiro {[}4H-chromene-4,5 `-isoxazolines] and related compounds: synthesis and reactivities / Sosnovskikh V. Ya.,Sizov A. Yu.,Usachev B. I.,Kodess M. I.,Anufriev V. A. // RUSSIAN CHEMICAL BULLETIN. - 2006. - V. 55, l. 3. - P. 535-542.

ISSN/EISSN:

1066-5285 / нет данных

Type:

Article

Abstract:

Reactions of chromones with methyl ketoximes in the presence of lithium diisopropylamide follow the nucleophilic 1,2-addition mechanism to give spiro{[}4H-chromene-4,5'-isoxazolines] in good yields. The isoxazoline ring in spiro{[}4H-chromene-4,5'-isoxazolines] undergoes opening under the action of conc. H2SO4, yielding alpha,beta-unsaturated oximes. Their nitrosation and bromination lead to the corresponding spiroisoxazolines, while the Beckmann rearrangement, to a,p-unsaturated amides. The latter are also formed directly from spiro{[}4H-chromene-4,5'-isoxazolines] under the action of PCl5. N-Substituted acetophenone hydrazones in the presence of lithium diisopropylamide react at the C(4) atom of 2-trifluoromethylchromone, while acetophenone anil under the same conditions, at the C(2) atom.

Author keywords:

chromones; dilithio oximes and dilithio hydrazones; spiro{[}4H-chromene-4,5 `-isoxazolines]; and spiro{[}4H-chromone-4,5 `-pyrazolines]; alpha,beta-unsaturated oximes and amides; Beckmann rearrangemen REGIOSPECIFIC SYNTHESIS; 3-SUBSTITUTED 5-ALKYLISOXAZOLES; DILITHIATED C(ALPHA),O-OXIMES; OXIME DIANIONS; ISOXAZOLES; 2-POLYFLUOROALKYLCHROMONES; DERIVATIVES; CHROMONES; LITHIATION; PYRAZOLES

DOI:

10.1007/s11172-006-0288-x

Web of Science ID:

ISI:000239714700019

Соавторы в МНС:

Другие поля

Поле	Значение
Month	MAR
Publisher	CONSULTANTS BUREAU/SPRINGER
Address	233 SPRING ST, NEW YORK, NY 10013 USA
Language	English
Keywords-Plus	REGIOSPECIFIC SYNTHESIS; 3-SUBSTITUTED 5-ALKYLISOXAZOLES; DILITHIATED C(ALPHA),O-OXIMES; OXIME DIANIONS; ISOXAZOLES; 2-POLYFLUOROALKYLCHROMONES; DERIVATIVES; CHROMONES; LITHIATION; PYRAZOLES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Multidisciplinary
Author-Email	Vyacheslav.Sosnovskikh@usu.ru
Number-of-Cited-References	29
Usage-Count-Last-180-days	2
Usage-Count-Since-2013	19
Journal-ISO	Russ. Chem. Bull.
Doc-Delivery-Number	073AN