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1、1799SynthesisofMono-andN,N-DisubstitutedThioureasandN-AcylthioureasSynthesisofSubstitutedThioureasandAlanR.Katritzky,*NataliyaKirichenko,BorisV.Rogovoy,JeremyKister,HuiTaoN-AcylthioureasCenterforHeterocyclicCompounds,DepartmentofChemistry,UniversityofFlo
2、rida,Gainesville,Florida32611-7200,USAFax+1(352)3929199;E-mail:katritzky@chem.ufl.eduReceived12February2004SAbstract:1-Benzotriazole-1-carbothioamide(2),preparedfrom1-Si(NCS)4cyanobenzotriazole(1)andhydrogensulfide,reactswithaminestoPhCONCSH2NNH2givethio
3、ureas3a–e.Reactionsof(benzotriazol-1-yl)carboximid-1.R2NHamides4a–d,f–jandacyl-5a–f,i–korarylaminocarbonyl-5g,h(ii)(iii)2.H+(iv)1.R1NHR1NH(benzotriazol-1-yl)carboximidamideswithhydrogensulfidegive222.-OHthecorrespondingthioureas3a–d,f–j,andN-acylthiourea
4、s6a–f,i–korN-carbamoylthioureas6g,h,respectively.SKeywords:thioureas,benzotriazole,acylations,nucleophilicsub-R1=Aryl(i)1(v)R1NHRR1NCSstitution,substituenteffects2MSCNH2NNR2NHM=Na,NHR24Thioureamoietiesareimportantchemicalbuildingblocks(vii)(vi)CS2thathav
5、enumerouschemicalandpharmaceuticalapplica-LiAlHSHorHg(OAc)2tions.Forexample,recentreportsdescribethioureaderiv-R1H2S/NH3NH31NNativesasefficientguanylatingagentsbothinsolutionandR1NH22R2onsolidsupport.ThermaldecompositionofN-arylthio-ureasgivesarylisothio
6、cyanates.3Oxidationofarylthio-Scheme1ureaswithleadtetraacetate4oriodicacid5affordsarylcyanamides.Thioureascondensewitha-halocarbonylAcylthioureasarevaluablestartingmaterialsfornumer-compoundstoafford2-amino-1,3-thiazoles.6Benzothiaz-oustransformations:ac
7、ylthioureaswereusedfortheprep-olescanbepreparedfromarylthioureasinthepresenceofarationoffour-,24five-,25six-25c,26andseven-27memberedbromine.7Solid-phaseBiginellipyrimidinesynthesis8andheterocyclicringsystems.N,N-Dialkyl-N¢-ac-synthesisofimidazolonederiv
8、atives9usingresin-boundyl(aroyl)thioureasareefficientligandsfortheseparationthioureashavebeenreported.Theusesofthioureastoandrefinementofplatinumgroupmetals(Pd,Rh,Ru,Ir,101112make1,3-thiazines,1,3-diazines,1,3-quinazolines
