An Efficient One-Pot Procedure for Preparation of 2,4(1H,3H)-Quinazolinediones and 2-Thioxoquinazolinone Derivatives Under Microwave Irradiation

Abstract An efficient one-pot synthesis of 2,4(1H,3H)-quinazolinediones and 2-thioxoquinazolinone derivatives are given by the condensation of isatoic anhydride, primary amine and urea or thiourea in the absence of organic or inorganic reagents under microwave irradiation.

[1]  J. Azizian,et al.  MICROWAVE-INDUCED ONE-POT SYNTHESIS OF SOME NEW SPIRO[3H-INDOLE-3,5′(4′H)-[1,2,4]- TRIAZOLINE]-2-ONES , 2001 .

[2]  J. V. Eynde,et al.  QUATERNARY AMMONIUM SALT-ASSISTED ORGANIC REACTIONS IN WATER: ALKYLATION OF PHENOLS , 2001 .

[3]  M. Mehrdad,et al.  Rearrangement of 4-imino-(1H,4H)-3,1-benzoxazine-2-ones to 2,4-quinazolinediones via an isocyanate carboxamide intermediate , 2000 .

[4]  U. Möllmann,et al.  Relationships Between the Chemical Structure of Substances and Their Antimycobacterial Activity Against Atypical Strains. Part 18. 3-Phenyl-2H-1,3-benzoxazine-2,4(3H)-diones and Isosteric 3-Phenylquinazoline-2,4(1H,3H)-diones , 1999 .

[5]  P. Molina,et al.  New methodology for the preparation of quinazoline derivatives via tandem aza-Wittig/heterocumulene-mediated annulation. Synthesis of 4(3H)-quinazolinones, benzimidazo[1,2-c]quinazolines, quinazolino[3,2-a]quinazolines and benzothiazolo[3,2-c]quinazolines , 1989 .

[6]  P. Molina,et al.  Heterocyclic synthesis via a tandem aza-Wittig reaction/heterocumulene-mediated annulation reaction. New methodology for the preparation of quinazoline derivatives. , 1988 .

[7]  R. A. Olofson,et al.  Reactions of anthranilium salts with nucleophiles: adduct formation and rearrangement , 1984 .

[8]  G. Tennant,et al.  The chemistry of nitro-compounds. Part II. The scope and mechanism of the base-catalysed transformations of someNN-disubstituted o-nitrobenzamides , 1972 .

[9]  T. Kappe,et al.  Synthesen von Heterocyclen, 89. Mitt.: ber Reaktionen des Isatosureanhydrids mit Harnstoff-und Thioharnstoff-Derivaten , 1967 .

[10]  M. Kurihara,et al.  Molecular Rearrangement in Polyphosphoric Acid. II. The Conversion of 1,2-Dihydro-2-phenylimino-4H-3, 1-benzoxazin-4-one to 3-phenyl-2, 4(1H, 3H)-quinazolinedione , 1966 .

[11]  K. Shimada,et al.  [STUDIES ON BENZOHETEROCYCLIC COMPOUNDS. I. SYNTHESIS AND PHARMACOLOGICAL ACTION OF QUINAZOLONE DERIVATIVES]. , 1965, Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan.

[12]  Bernard Taub,et al.  3-Substituted 2,4-Quinazolinediones , 1961 .