The Remarkable Cooperative Effect of a Bronsted-Acidic Ionic Liquid in the Cyclization of 2-Aminobenzamides with Ketones / Das Sudarshan,Santra Sougata,Jana Sourav,Zyryanov Grigory V.,Majee Adinath,Hajra Alakananda // EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - 2017. - V. , l. 33. - P. 4955-4962.

ISSN/EISSN:

1434-193X / 1099-0690

Type:

Article

Abstract:

An unprecedented role of an imidazolium Bronsted acidic ionic liquid was found in the formation of 2,2-disubstituted quinazolin-4(1H)-one derivatives; both the C2-H of the imidazolium moiety and an acidic proton were necessary and simultaneously took part in the catalysis. A library of quinazolin4( 1H)-ones was prepared from readily available ketones and 2-aminobenzamides; excellent yields were obtained through simple crystallization under solvent-free conditions with lower E factors. The catalyst could be reused over five consecutive runs without any significant loss in catalytic activity. This method produces only water as a byproduct and represents a green synthetic protocol. A clean reaction, no chromatographic purification, easily accessible reactants, a metal-free and solvent-free process, and environmentally friendly reaction conditions are the notable advantages of this procedure. The possible role of the C2-H of the imidazolium moiety in catalysis was studied by mass spectrometry.

Author keywords:

Bronsted acids; Ionic liquids; Nitrogen heterocycles; Sustainable chemistry; Mass spectrometry ONE-POT SYNTHESIS; APROTIC IMIDAZOLIUM ZWITTERION; CATALYTIC ASYMMETRIC-SYNTHESIS; SOLVENT-FREE CONDITIONS; EFFICIENT SYNTHESIS; MOLTEN-SALT; REGIOSELECTIVE SYNTHESIS; COMBINATORIAL SYNTHESIS; MEDIATED SYNTHESIS; TANDEM REACTION

DOI:

10.1002/ejoc.201700966

Web of Science ID:

ISI:000409861000011

Соавторы в МНС:

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Другие поля

Поле	Значение
Month	SEP 8
Publisher	WILEY-V C H VERLAG GMBH
Address	POSTFACH 101161, 69451 WEINHEIM, GERMANY
Language	English
EISSN	1099-0690
Keywords-Plus	ONE-POT SYNTHESIS; APROTIC IMIDAZOLIUM ZWITTERION; CATALYTIC ASYMMETRIC-SYNTHESIS; SOLVENT-FREE CONDITIONS; EFFICIENT SYNTHESIS; MOLTEN-SALT; REGIOSELECTIVE SYNTHESIS; COMBINATORIAL SYNTHESIS; MEDIATED SYNTHESIS; TANDEM REACTION
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	alakananda.hajra@visva-bharati.ac.in
Funding-Acknowledgement	Department of Science and Technology (DST), GoWB {[}700(Sanc.)/ST/P/ST/4G-2/2014]; Russian Science Foundation, Russia {[}16-43-02020]
Funding-Text	A.H. acknowledges financial support from the Department of Science and Technology (DST), GoWB {[}Grant no. 700(Sanc.)/ST/P/S\&T/4G-2/2014]. S.S. is thankful to the Russian Science Foundation, Russia (Ref. \# 16-43-02020) for funding. We are also thankful to Department for Science and Technology, Fund for Improvement of S \& T Infrastructure (DST-FIST) and University Grants Commission (UGC)-SAP.
Number-of-Cited-References	87
Usage-Count-Last-180-days	12
Usage-Count-Since-2013	12
Journal-ISO	Eur. J. Org. Chem.
Doc-Delivery-Number	FG1YD