Bronsted acidic ionic liquid-catalyzed tandem reaction: an efficient approach towards regioselective synthesis of pyrano{[}3,2-c]coumarins under solvent-free conditions bearing lower E-factors / Mahato Sachinta,Santra Sougata,Chatterjee Rana,Zyryanov Grigory V.,Hajra Alakananda,Majee Adinath // GREEN CHEMISTRY. - 2017. - V. 19, l. 14. - P. 3282-3295.

ISSN/EISSN:

1463-9262 / 1463-9270

Type:

Article

Abstract:

1-Butane sulfonic acid-3-methylimidazolium tosylate, {[}BSMIM]OTs, is found to be a remarkable catalyst for the tandem cyclization of 4-hydroxycoumarin with chalcones for the syntheses of pyrano{[}3,2-c]coumarins under solvent-free conditions. The developed protocol is applicable for the construction of biologically important pyranocoumarins from easily accessible chalcones having various substituents. This reaction possibly proceeds through Michael addition followed by cyclization. The feasibility of catalyst recycling is also demonstrated. This method produces only water as the byproduct and represents a green synthetic protocol. The catalytic reaction proceeded very smoothly under solvent-free conditions and showed high regioselectivity. Clean reaction, non-chromatographic purification technique, easily accessible reactants, and metal and solvent-free and environmentally friendly reaction conditions are the notable advantages of this procedure. In addition, this method shows lower E-factors.

Author keywords:

SELECTIVE ACETYLCHOLINESTERASE INHIBITORS; PENICILLIUM SP FO-4259; MEDIATED SYNTHESIS; 1,3-DICARBONYL COMPOUNDS; ORGANIC-SYNTHESIS; CASCADE REACTIONS; MICHAEL ADDITION; ARISUGACIN-A; MOLTEN-SALT; DERIVATIVES

DOI:

10.1039/c7gc01158j

Web of Science ID:

ISI:000405685000011

Соавторы в МНС:

Другие поля

Поле	Значение
Month	JUL 21
Publisher	ROYAL SOC CHEMISTRY
Address	THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND
Language	English
EISSN	1463-9270
Keywords-Plus	SELECTIVE ACETYLCHOLINESTERASE INHIBITORS; PENICILLIUM SP FO-4259; MEDIATED SYNTHESIS; 1,3-DICARBONYL COMPOUNDS; ORGANIC-SYNTHESIS; CASCADE REACTIONS; MICHAEL ADDITION; ARISUGACIN-A; MOLTEN-SALT; DERIVATIVES
Research-Areas	Chemistry; Science \& Technology - Other Topics
Web-of-Science-Categories	Chemistry, Multidisciplinary; GREEN \& SUSTAINABLE SCIENCE \& TECHNOLOGY
Author-Email	adinath.majee@visva-bharati.ac.in
Funding-Acknowledgement	DST-RSF Major Research Project {[}INT/RUS/RSF/P-08]; Russian Science Foundation - Russia {[}16-43-02020]
Funding-Text	A. Majee acknowledges financial support from the DST-RSF Major Research Project (Ref. No. INT/RUS/RSF/P-08). S. Santra and G. V. Zyryanov acknowledge the Russian Science Foundation - Russia (Ref. \# 16-43-02020) for funding. We are thankful to the DST-FIST and UGC-SAP programmes.
Number-of-Cited-References	91
Usage-Count-Last-180-days	7
Usage-Count-Since-2013	7
Journal-ISO	Green Chem.
Doc-Delivery-Number	FA8GU