Baran, Newhouse, Seiple Essentials of Heterocyclic ...

1 Heterocyclic ChemistryBaran, Newhouse, SeipleEssentials of Heterocyclic chemistry -IVIsoindoles:NPhthalOPhN2H4 EtOHNHPhPhOPhONMePhPhMeNH2 NaBH4 PhOPhOMeMeSPhPhP4S10 SMeMeOOSMeMeMeMeOHOHMeMeSPhPhCHOOHCSOOPh PhOMeMeOi. ii. O3 RROHOOClOCO2 HHOOCHOCO2 HOAc2O, NaOAc,AcOH, ONMeOMeMeBF3, AcOHOHIOHIOOMeMeOPd(OAc)2, basethen BF3 OCO2 MeTIPSRPd(OAc)2, baseORSEtOOEtSPPAFCHOSHSCO2 MeNaHBenzo[c]thiophenes:Benzothiophenes: Benzofurans:HO2 CNHRRRNRRRODICEtO2 CNHRRRNHRRRLHMDSOStButBuMgClNOPhPhNArArn BuLiCO2tBuRNRTMSLDABeta-lactams:RO2 CRBrNArRZnHFNaOH TIPSMeMeCO2 MeOxetanes:ORR1R2R3 ORR1R2R3h OHR1 RMsOnBuNOAcSSObase Paterno-B chi ReactionOR1 RThiazoles and Isothiazoles:MeXOX = N2 or Cl,HMeSH2N+NSMeMeHantzsch Thiazole SynthesisXOSMeSH2N+NSi.

2 Aq. ROHii. Li/NH3R1SR2 OONH4 OAcNSMeMeRSHNSTosMICRHOi. Na2S2O3ii. NH3 NSRO2 CMeNH2i. TsNCSii. I2, pyNNHTsRO2 CMeImidazoles:OOBrH2 NOH+NH3, NHNR1 OBrNH2H2 NNR2 NHN+R1 NHR2 RHNHTosMICNHNRiPrOBrCHONH2 ArNR+K2CO3 ArHNNOHCCNEtOOEti. ArNH2 TsN(Na)Clii. H+, NNNHTsArThiadiazoles:MeNHNCO2 HCO2 EtSOCl2 SNNHO2 CNNHTsCl3CS8, Na2SH2 OSNNNaSPhH2 NSI2 NNSPhPhMeNH2 HNNSMeCCl3 SClNaOHClNNOPhNNSPhP4S10 RHNSNHNH2(OEt)3 CHNNSRHNH2 NNH2 NNSS2Cl2 PhPhOONNSPhPhSNH2H2 NOOH++NSNSNSClClClPhthNNNSNPhthOOvon Leusen Thiazole SynthesisRobinson Gabriel Thiazole SynthesisNNMe2 NNMe2H2S, MeOHNNSNHNR1R1 ONHR+ [O]XClClSR1R1 NOHNR2 ClPhNNPhR2R1R1 Lantos Eggleston Imidazole SynthesisHeterocyclic ChemistryBaran, Newhouse, SeipleEssentials of Heterocyclic chemistry -IVTop 15 Brand-Name Pharmaceuticals with Heterocycles.

3 ONHHOMeOMeOOHNMeONCO2 HOHCO2 HMeMeSHHNH2 NOHONOHOMeNNNClPhNOHNClClNOHOMeOPhOHOSO2 NHHNH2NO2 SClMeCO2 HNNHH2 NPhOOHSOHNClNO2 NHO2 CNNHEtO2 CBnMeOSNOAcONMe2 MeOCO2HH2NO2 SClHNOCO2 HNFNHNOH ydrochlorothiazide2006 rank: 302006 sales: $ : fluid buildupONCNMe2 FMeMeMeOMeMeHOOOHONOHHO2 CMeMePhPhHONNBnEtOCPhCO2 HNH2 NHNCO2 HBnOOSNMeONHNMeOMeMeCO2 MeClNSNHOOOFC ephalexin2006 rank: 312006 sales: $ : antibioticClonazepam2006 rank: 332006 sales: $ : seizures, panicQuinapril2006 rank: 312006 sales: $ : hypertensionDiltiazem2006 rank: 382006 sales: $ : hypertension, anginaFurosemide2006 rank: 422006 sales: $ : edema, hypertensionCiprolfloxacin HCl2006 rank: 432006 sales: $ : ulcersCitalopram HBr2006 rank: 452006 sales: $ : depressionParoxetine2006 rank: 142006 sales: $ : depression, panicAlprazolam2006 rank: 182006 sales: $ : anxiety, panicLorazepam2006 rank: 252006 sales: $ : anxietyWarfarin2006 rank: 262006 sales: $ : hypertensionFexofenadine2006 rank: 72006 sales: $ : allergiesFentanyl2006 rank: 82006 sales: $ : painLisinopril2006 rank: 92006 sales: $ : hypertensionClopidogrel2006 rank: 132006 sales: $ : stroke, heart attackHydrocodone/ Acetaminophen2006 rank: 12006 sales: $ : painSimvastatin2006 rank: 22006 sales: $ : cholesterolOxycodone2006 rank: 42006 sales: $ : painOmeprazole2006 rank: 122006 sales: $.

4 HeartburnAmoxicillin/Pot Clav2006 rank: 62006 sales: $ : antibioticOMeOOOHNMeNPhONHPhFMeMeHO2 CHOHOL ipitor (Pfizer)2006 rank: 12006 sales: $ : high LDL cholestorolNMeMeOMeSOHNNOMeNexium (Astra-Zeneca)2006 rank: 22006 sales: $ : heartburn/esophigitisNNHSONMeOF3 CPrevacid (TAP)2006 rank: 32006 sales: $ : gastric refluxNClSMeMeHOHO2 CSingulair (Merck)2006 rank: 52006 sales: $ : asthmaSNCO2 MeClPlavix (BMS)2006 rank: 72006 sales: $ : stroke/heart attackClNHONH2 MeEtO2 CMeO2 CNorvasc (Pfizer)2006 rank: 92006 sales: $ : hypertension/anginaNSONHNOFFMeOOMeProton ix (Wyeth)2006 rank: 122006 sales: $ : esophagitisNNMeMeNMe2 OAmbien (Sanofi Aventis)2006 rank: 132006 sales: $ : insomniaNONHSOOMeNONHSOOMeNActos (Eli Lilly)2006 rank: 142006 sales: $ : type 2 diabetesAvandia (GSK)2006 rank: 172006 sales: $ : type 2 diabetesNNOMeNNOFR isperdal (J & J)2006 rank: 182006 sales: $ : schizophrenia/bipolar maniaNHNSNNMeMeZyprexa (Eli Lilly)2006 rank: 192006 sales: $ : schizophrenia/bipolar maniaMeMeMeOMeMeHOOOHOZ ocor (Merck)2006 rank: 82006 sales: $ : high LDL CholestorolONCMe2 NFSNNNOOHS eroquel (Astra-Zeneca)2006 rank: 112006 sales: $ : schizophrenia/bipolar maniaLexapro (Forest)2006 rank: 102006 sales: $ : depression and anxietyOOOOOMeMeMeMeOSOONH2 Topamax (J & J)2006 rank: 202006 sales: $.

5 Seizures and migranesTop 21 Generic Pharmaceuticals with Heterocycles.