Reactions of 2(3)-ethoxycarbonyl-5,6,7,8-tetrafluorochromones with methylamine / Shcherbakov KV,Burgart VV,Saloutin VI // RUSSIAN CHEMICAL BULLETIN. - 2005. - V. 54, l. 9. - P. 2157-2162.

ISSN/EISSN:

1066-5285 / нет данных

Type:

Article

Abstract:

2-Ethoxycarbonyl-5,6,7,8-tetraflluorochromone reacts with methylamine differently, depending on the solvent nature and the amount of the amine: in DMSO and MeCN, the fluorine atom at the C(7) atom is initially replaced and then the C(2) and/or C(9) are attacked, while in ethanol, the reaction involves the C(2) atom with opening of the pyrone ring. The reaction of 3-ethoxycarbonyl-5,6,7,8-tetrafluoro-2-methylchromone with methylamine results, regardless of the solvent, in opening of the chromone ring and the formation of intermediate ethyl 3-(3,4,5,6-tetrafluoro-2-hydroxyphenyl)-2-(1-methylamino)ethylidene-3-ox opropionate, which undergoes intramolecular cyclization to give 5,6,7,8-tetrafluoro-3-(1-methylamino)ethylidene-3,4-dihydro-2H-benzopyra n-2,4-dione.

Author keywords:

chromone; methylamine; nucleophilic substitution; ring opening; chromone-coumarin rearrangement N-NUCLEOPHILES; CHROMONES

DOI:

10.1007/s11172-006-0091-8

Web of Science ID:

ISI:000236859600022

Соавторы в МНС:

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Другие поля

Поле	Значение
Month	SEP
Publisher	CONSULTANTS BUREAU/SPRINGER
Address	233 SPRING ST, NEW YORK, NY 10013 USA
Language	English
Keywords-Plus	N-NUCLEOPHILES; CHROMONES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Multidisciplinary
Author-Email	saloutin@ios.uran.ru
Number-of-Cited-References	13
Journal-ISO	Russ. Chem. Bull.
Doc-Delivery-Number	033OY