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Facile Non-Transition Metal-Catalyzed Synthesis of 2-Thioxo-2,3-Dihydroquinazolin-4(1H)-One Derivatives Via One-Pot Multicomponent Reactions Publisher



Bahadorikhalili S1 ; Rahimzadeh G2 ; Kianmehr E2 ; Ansari S3 ; Hamedifar H3 ; Mahdavi M4
Authors
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Authors Affiliations
  1. 1. Institute of Mechanics, Iranian Space Research Center, Shiraz, Iran
  2. 2. School of Chemistry, College of Science, University of Tehran, P. O. Box:14155-6455, Tehran, Iran
  3. 3. CinnaGen Medical Biotechnology Research Center, Alborz University of Medical Sciences, Karaj, Iran
  4. 4. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, 14176, Iran

Source: ChemistrySelect Published:2019


Abstract

In this paper, a novel method is introduced for the synthesis of 3-substituted 2-thioxo-2,3-dihydroquinazolin-4(1H)-one derivatives. This methodology is based on the multicomponent one-pot reaction of isatoic anhydride, amines, chloroform and sulfur in basic conditions. The products are obtained in highest efficiency when the reaction is performed in 1,4-dioxane as the solvent in the presence of potassium tert-butoxide as the base. The reaction showes to be efficient and simple for the preparation of these compounds. In addition, this method is general and different aromatic or aliphatic amines are used and the desired products are isolated in high yields. A possible mechanism for the reaction is proposed, which consisted the dichlorocarbene formation under the basic conditions. © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim