One-Pot Quinazolin-4-yl-thiourea Synthesis via N-(2-Cyanophenyl) benzimidoyl isothiocyanate 英文参考文献.docVIP

Molecules 2001, 6, 588-602 molecules ISSN 1420-3049 One-Pot Quinazolin-4-yl-thiourea Synthesis via N-(2-Cyano- phenyl)benzimidoyl isothiocyanate Fathalla, W. , ?ajan, M. , Marek, J. and Pazdera, P. * 1 1,2 3 1, 1 Department of Organic Chemistry, Faculty of Science, Masaryk University, Brno, Czech Republic, Tel.: +420 5 Fax: +420 5 2 Laboratory of Biomolecular Structure and Dynamics, Faculty of Science, Masaryk University, Brno, Czech Republic. 3 Department of Inorganic Chemistry, Masaryk University, 611 37 Brno, Czech Republic. *Author to whom correspondence should be addressed; E-mail: pazdera@chemi.muni.cz Received: 10 November 2000; in revised form 22 May 2001 / Accepted: 23 May 2001 / Published: 30 June 2001 Abstract: 1-substituted-3-(2-phenylquinazolin-4-yl) thioureas (7) were produced by an intramolecular cycloaddition reaction of 1-substitued-3-[(2-cyanophenyl- imino)phenylmethyl] thioureas (3). These compounds in turn were prepared by the reaction of N-(2-cyanophenyl)benzimidoyl isothiocyanate (2) with primary amines. The structures of products 7 were confirmed by FTIR, 1H-NMR, 13C-NMR, mass spectroscopy and X-ray crystallography. Keywords: 1-(2-phenylquinazolin-4-yl)-3-substituted thioureas; 1-[(2-cyano- phenylimino)phenylmethyl]-3-substituted thioureas; N-(2-cyanophenyl)- benzimidoyl isothiocyanate; one-pot synthesis; amidinoyl isothiocyanates. Introduction This work is a continuation of our studies of the competition between the sulfur and nitrogen atoms in a thioamide moiety towards intermolecular and intramolecular reactions with electrophiles [1-3]. The intramolecular cycloaddition reaction of the product formed in situ by addition of  Molecules 2001, 6 589 secondary amines to N-(2-cyanophenyl)benzimidoyl isothiocyanate affords 1,1-disubstituted-3-(2- phenyl-3H-quinazolin-4-ylid