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1、Molecules2001,6,588-602moleculesISSN1420-3049http://www.mdpi.orgOne-PotQuinazolin-4-yl-thioureaSynthesisviaN-(2-Cyano-phenyl)benzimidoylisothiocyanateFathalla,W.,Čajan,M.,Marek,J.andPazdera,P.*11,231,1DepartmentofOrganicChemistry,FacultyofScience,MasarykUniversity,Brno
2、,CzechRepublic,Tel.:+420541129305,Fax:+420541211214,2LaboratoryofBiomolecularStructureandDynamics,FacultyofScience,MasarykUniversity,Brno,CzechRepublic.3DepartmentofInorganicChemistry,MasarykUniversity,61137Brno,CzechRepublic.*Authortowhomcorrespondenceshouldbeaddresse
3、d;E-mail:pazdera@chemi.muni.czReceived:10November2000;inrevisedform22May2001/Accepted:23May2001/Published:30June2001Abstract:1-substituted-3-(2-phenylquinazolin-4-yl)thioureas(7)wereproducedbyanintramolecularcycloadditionreactionof1-substitued-3-[(2-cyanophenyl-imino)p
4、henylmethyl]thioureas(3).ThesecompoundsinturnwerepreparedbythereactionofN-(2-cyanophenyl)benzimidoylisothiocyanate(2)withprimaryamines.Thestructuresofproducts7wereconfirmedbyFTIR,1H-NMR,13C-NMR,massspectroscopyandX-raycrystallography.Keywords:1-(2-phenylquinazolin-4-yl
5、)-3-substitutedthioureas;1-[(2-cyano-phenylimino)phenylmethyl]-3-substitutedthioureas;N-(2-cyanophenyl)-benzimidoylisothiocyanate;one-potsynthesis;amidinoylisothiocyanates.IntroductionThisworkisacontinuationofourstudiesofthecompetitionbetweenthesulfurandnitrogenatomsin
6、athioamidemoietytowardsintermolecularandintramolecularreactionswithelectrophiles[1-3].Theintramolecularcycloadditionreactionoftheproductformedinsitubyadditionof
Molecules2001,6589secondaryaminestoN-(2-cyanophenyl)benzimidoylisothiocyanateaffords1,1-disubstituted-3-(2-p
7、henyl-3H-quinazolin-4-ylidene)thioureas[3].Thesecyclicproductsareformedviaaone-potreactionsequenceincludingcyclization,Dimrothrearrangementandtautomerisationsteps,asreportedin[3].ResultsandDiscussionTheextensionofsuchareactiontoincludeprimaryamines,anilines,heterocycli
8、camines,andadamantanaminederivativesisnowreportedinthispaper.ThereactionproceedsbytheadditionofprimaryaminestoN-(2-cy
