NDLI: Convenient synthesis of 2,3-disubstituted quinazolin-4(3H)-ones and 2-styryl-3-substituted quinazolin-4(3H)-ones: applications towards the synthesis of drugs

Content Provider	Royal Society of Chemistry (RSC)
Author	Nautiyal, Manesh Sharma, Himanshu Adane, Legesse Kumar, Dinesh Pancholia, Sahaj Chakraborti, Asit K. Meena, Prahlad K. Jadhavar, Pradeep S.
Copyright Year	2015
Abstract	Simple, convenient, and green synthetic protocols have been developed for the one pot synthesis of 2,3-disubstituted quinazolin-4(3H)-ones and 2-styryl-3-substituted quinazolin-4(3H)-ones under catalyst and solvent free conditions. The multicomponent reaction (3-MCR) involving isatoic anhydride, an amine, and orthoester afforded the 2,3-disubstituted quinazolin-4(3H)-ones in excellent yields under classical heating at 120 °C for 5 h or under microwave irradiation at 140 °C for 20–30 min. The use of ammonium acetate instead of the amine provides the 2-substituted quinazolin-4(3H)-ones. The reactions are compatible with various substituted isatoic anhydrides, aryl/heteroaryl/alkyl/cycloalkyl amines, and orthoesters. The strategies are extended to the one pot tandem condensation involving isatoic anhydride, an amine, orthoester, and aldehyde to afford highly functionalized (E)-3-aryl/heteroaryl-2-styrylquinazolin/(2-(heteroaryl)vinyl)quinazolin-4(3H)-ones. The applications of the methodologies are demonstrated through the synthesis of various drugs which act on the central nervous system such as methaqualone, mebroqualone, mecloqualone, piriquialone, and diproqualone.
Starting Page	30819
Ending Page	30825
Page Count	7
File Format	HTM / HTML PDF
ISSN	20462069
Volume Number	5
Issue Number	39
Journal	RSC Advances
DOI	10.1039/c5ra03888j
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Quaternary ammonium cation Methaqualone Mebroqualone Diproqualone Isatoic anhydride Central nervous system Microwave chemistry Mecloqualone Aldehyde Multi-component reaction Classical mechanics Alkyl Orthoester Aryl Solvent
Content Type	Text
Resource Type	Article
Subject	Chemistry Chemical Engineering

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