Synthesis of functionalized 2-salicyloylfurans, furo{[}3,2-b]chromen-9-ones and 2-benzoyl-8H-thieno{[}2,3-b]indoles by one-pot cyclizations of 3-halochromones with beta-ketoamides and 1,3-dihydroindole-2-thiones / Savych Iryna,Glaesel Tim,Villinger Alexander,Sosnovskikh Vyacheslav Ya.,Iaroshenko Viktor O.,Langer Peter // ORGANIC \& BIOMOLECULAR CHEMISTRY. - 2015. - V. 13, l. 3. - P. 729-750.

ISSN/EISSN:

1477-0520 / 1477-0539

Type:

Article

Abstract:

Functionalized 2-salicyloylfurans and 2-benzoyl-8H-thieno{[}2,3-b]indoles were prepared under mild conditions by reaction of 3-halochromones with beta-ketoamides and 1,3-dihydroindole-2-thiones, correspondently. The subsequent oxidative cyclization of the products resulted in formation of the corresponding furo{[}3,2-b]chromen-9-ones. These molecules could also be directly prepared from 3-halochromones using a one-pot protocol. The cyclization reactions reported herein are mechanistically surprising as they proceed via the oxygen and not via the (more nucleophilic) nitrogen atom of the beta-ketoamide.

Author keywords:

C-H FUNCTIONALIZATION; LEPTOSPHAERIA-MACULANS; EFFICIENT SYNTHESIS; PHYTOALEXINS BRASSILEXIN; 1,3-DICARBONYL COMPOUNDS; REGIOSELECTIVE SYNTHESIS; CONJUGATE ADDITION; FACILE SYNTHESIS; RING-SYSTEM; CHROMONES

DOI:

10.1039/c4ob01730g

Web of Science ID:

ISI:000346483700012

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
EISSN	1477-0539
Keywords-Plus	C-H FUNCTIONALIZATION; LEPTOSPHAERIA-MACULANS; EFFICIENT SYNTHESIS; PHYTOALEXINS BRASSILEXIN; 1,3-DICARBONYL COMPOUNDS; REGIOSELECTIVE SYNTHESIS; CONJUGATE ADDITION; FACILE SYNTHESIS; RING-SYSTEM; CHROMONES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	iva108@googlemail.com peter.langer@uni-rostock.de
ResearcherID-Numbers	Iaroshenko, Viktor/I-6150-2015
Funding-Acknowledgement	State of Mecklenburg-Vorpommern; BMBF {[}03IS2081A]
Funding-Text	Financial support by the State of Mecklenburg-Vorpommern (scholarship for I. S.) and by the BMBF (REMEDIS project, grant no. 03IS2081A) is gratefully acknowledged.
Number-of-Cited-References	77
Usage-Count-Since-2013	21
Journal-ISO	Org. Biomol. Chem.
Doc-Delivery-Number	AW8AT