A novel redox reaction between 8-aza-5,7-dimethyl-2-trifluoromethylchromone and alkyl mereaptoacetates. Facile synthesis of CF3-containing 2-pyridone derivatives / Sosnovskikh VY,Barabanov MA,Usachev BI // JOURNAL OF ORGANIC CHEMISTRY. - 2004. - V. 69, l. 24. - P. 8297-8304.

ISSN/EISSN:

0022-3263 / нет данных

Type:

Article

Abstract:

8-Aza-5,7-dimethyl-2-trifluoromethylchromone reacts with alkyl mercaptoacetates in the presence of triethylamine to give pyrido derivatives of 2-oxa-7-thiabicyclo{[}3.2.1] octane, which undergo the reductive ring opening to alkyl 2-1{[}3-(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)-3-oxo-l(trifluorome thyl)propyllsulfanyllacetates.The latter can be also obtained directly from 8-aza-5,7dimethyl-2-trifluoromethylchromone and behave as the masked alpha,beta-unsaturated ketone, 4,6dimethyl-3-(4,4,4-trifluorobut-2-enoyl)pyridin-2(1H)-one. This compound was independently synthesized from 3-acetyl-4,6-dimethyl-2-pyridone, and its synthetic potential was studied. A wide variety of 2-pyridone derivatives containing the CF3 group have been prepared in good to moderate yields.

Author keywords:

BETA-TRIFLUOROMETHYL KETONES; TRIFLUOROACETALDEHYDE ETHYL HEMIACETAL; MERCAPTOACETATES; 2-POLYFLUOROALKYLCHROMONES; 1,1-BIS(DIMETHYLAMINO)-2,2,2-TRIFLUOROETHANE; 1,1,1-TRIFLUORO-2-PENTEN-4-ONE; 7-POLYFLUOROALKYLNORKHELLINS; GENERATION; IMINES

DOI:

10.1021/jo049117m

Web of Science ID:

ISI:000225341300017

Соавторы в МНС:

Другие поля

Поле	Значение
Month	NOV 26
Publisher	AMER CHEMICAL SOC
Address	1155 16TH ST, NW, WASHINGTON, DC 20036 USA
Language	English
Keywords-Plus	BETA-TRIFLUOROMETHYL KETONES; TRIFLUOROACETALDEHYDE ETHYL HEMIACETAL; MERCAPTOACETATES; 2-POLYFLUOROALKYLCHROMONES; 1,1-BIS(DIMETHYLAMINO)-2,2,2-TRIFLUOROETHANE; 1,1,1-TRIFLUORO-2-PENTEN-4-ONE; 7-POLYFLUOROALKYLNORKHELLINS; GENERATION; IMINES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	vyacheslav.sosnovskikh@usu.ru
Number-of-Cited-References	49
Usage-Count-Since-2013	3
Journal-ISO	J. Org. Chem.
Doc-Delivery-Number	874HK