Reactions of 3-acylchromones with dimethyl 1,3-acetonedicarboxylate and 1,3-diphenylacetone: one-pot synthesis of functionalized 2-hydroxybenzo-phenones, 6H-benzo{[}c]chromenes and benzo{[}c]coumarins / Iaroshenko Viktor O.,Savych Iryna,Villinger Alexander,Sosnovskikh Vyacheslav Ya.,Langer Peter // ORGANIC \& BIOMOLECULAR CHEMISTRY. - 2012. - V. 10, l. 47. - P. 9344-9348.

ISSN/EISSN:

1477-0520 / нет данных

Type:

Article

Abstract:

Reactions of 3-methoxalyl-, 3-polyfluoroacyl-and 3-aroylchromones with dimethyl 1,3-acetonedicarboxylate and 1,3-diphenylacetone in the presence of DBU proceed at the C-2 atom of the chromone system with pyrone ring-opening and subsequent formal {[}3 + 3] cyclocondensation to functionalized 2-hydroxybenzophenones, 6H-benzo{[}c]chromenes and benzo{[}c]coumarins, depending on the substituent at the 3-position. An NMR study and X-ray crystallographic analysis are reported. The compounds synthesized can be considered as promising scaffolds for the design of the novel UV-A/B and UV-B filters.

Author keywords:

1,3-BIS-SILYL ENOL ETHERS; NICOTINIC-ACID DERIVATIVES; 1,3-DICARBONYL COMPOUNDS; REGIOSELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; ALDOL REACTIONS; METHYLENE-COMPOUNDS; ACTIVE METHYLENE; NATURAL-PRODUCTS; DOMINO REACTIONS

DOI:

10.1039/c2ob07020k

Web of Science ID:

ISI:000311161900007

Соавторы в МНС:

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Другие поля

Поле	Значение
Publisher	ROYAL SOC CHEMISTRY
Address	THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND
Language	English
Keywords-Plus	1,3-BIS-SILYL ENOL ETHERS; NICOTINIC-ACID DERIVATIVES; 1,3-DICARBONYL COMPOUNDS; REGIOSELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; ALDOL REACTIONS; METHYLENE-COMPOUNDS; ACTIVE METHYLENE; NATURAL-PRODUCTS; DOMINO REACTIONS
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	viktor.iaroshenko@uni-rostock.de
Funding-Acknowledgement	Landesgraduirte
Funding-Text	Financial support by the Landesgraduirte (scholarships for I.S.) is acknowledged.
Number-of-Cited-References	66
Usage-Count-Since-2013	15
Journal-ISO	Org. Biomol. Chem.
Doc-Delivery-Number	038FZ