Synthesis of Diketohexenoic Acid Derivatives by Alkenylation of Indoles and Pyrroles with 4-Pyrones / Obydennov Dmitrii L.,Pan'kina Ekaterina O.,Sosnovskikh Vyacheslav Y. // JOURNAL OF ORGANIC CHEMISTRY. - 2016. - V. 81, l. 24. - P. 12532-12539.

ISSN/EISSN:

0022-3263 / нет данных

Type:

Article

Abstract:

A new synthesis of functionalized (Z)-6-hetaryl-2,4-dioxo-5-hexenoic acids based on acid-catalyzed alkenylation of indoles and pyrroles with derivatives of 5-substituted 4-pyrone-2-carboxylic acid in 37-82\% yields has been developed. Coupling between isochelidonic acid and indoles followed by decarboxylation afforded biologically important (E)-6-indolyl-2,4-dioxo-5-hexenoic acids. These ring-opening reactions proceed with high regioselectivity through nucleophilic attack at the C-6 position of the pyrone ring. Reactions of ethyl 6-indolyl-2,4-dioxo-5-hexenoate with nucleophiles are useful for the production of different beta-(indoly)vinyl-containing azaheterocycles.

Author keywords:

OXO KETENE DITHIOACETALS; C-H; RIBONUCLEASE-H; DIKETO ACID; DUAL INHIBITORS; HIV-1 INTEGRASE; 6-(TRIFLUOROMETHYL)COMANIC ACID; NONNUCLEOSIDE INHIBITORS; REGIOSELECTIVE SYNTHESIS; REVERSE-TRANSCRIPTASE

DOI:

10.1021/acs.joc.6b02364

Web of Science ID:

ISI:000390180100050

Соавторы в МНС:

Другие поля

Поле	Значение
Month	DEC 16
Publisher	AMER CHEMICAL SOC
Address	1155 16TH ST, NW, WASHINGTON, DC 20036 USA
Language	English
Keywords-Plus	OXO KETENE DITHIOACETALS; C-H; RIBONUCLEASE-H; DIKETO ACID; DUAL INHIBITORS; HIV-1 INTEGRASE; 6-(TRIFLUOROMETHYL)COMANIC ACID; NONNUCLEOSIDE INHIBITORS; REGIOSELECTIVE SYNTHESIS; REVERSE-TRANSCRIPTASE
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	dobydennov@mail.ru
Funding-Acknowledgement	Russian Foundation for Basic Research {[}14-03-00179]
Funding-Text	This work was supported financially by the Russian Foundation for Basic Research (Grant 14-03-00179). Thanks also to Alisa Vlasova for her help in this work.
Number-of-Cited-References	73
Usage-Count-Last-180-days	2
Usage-Count-Since-2013	5
Journal-ISO	J. Org. Chem.
Doc-Delivery-Number	EF2UC