Applied Organic Chemistry: Reaction Mechanisms and Experimental Procedures in Medicinal Chemistry PDF
Preview Applied Organic Chemistry: Reaction Mechanisms and Experimental Procedures in Medicinal Chemistry
AppliedOrganicChemistry Applied Organic Chemistry ReactionMechanismsandExperimentalProceduresin MedicinalChemistry SuryaK.De Volume1 Applied Organic Chemistry ReactionMechanismsandExperimentalProceduresin MedicinalChemistry SuryaK.De Volume2 Author AllbookspublishedbyWiley-VCH arecarefullyproduced.Nevertheless, Dr.SuryaK.De authors,editors,andpublisherdonot SupraSciences warranttheinformationcontainedin SanDiego,CA thesebooks,includingthisbook,to UnitedStates befreeoferrors.Readersareadvised tokeepinmindthatstatements,data, CoverImage: illustrations,proceduraldetailsorother ©enot-poloskun/Getty itemsmayinadvertentlybeinaccurate. Images LibraryofCongressCardNo.: appliedfor BritishLibraryCataloguing-in-Publication Data Acataloguerecordforthisbookis availablefromtheBritishLibrary. Bibliographicinformationpublishedby theDeutscheNationalbibliothek TheDeutscheNationalbibliotheklists thispublicationintheDeutsche Nationalbibliografie;detailed bibliographicdataareavailableonthe Internetat<http://dnb.d-nb.de>. ©2021WILEY-VCHGmbH,Boschstr. 12,69469Weinheim,Germany Allrightsreserved(includingthoseof translationintootherlanguages).No partofthisbookmaybereproducedin anyform–byphotoprinting, microfilm,oranyothermeans–nor transmittedortranslatedintoa machinelanguagewithoutwritten permissionfromthepublishers. Registerednames,trademarks,etc.used inthisbook,evenwhennotspecifically markedassuch,arenottobe consideredunprotectedbylaw. PrintISBN:978-3-527-34785-8 ePDFISBN:978-3-527-82815-9 ePubISBN:978-3-527-82817-3 oBookISBN:978-3-527-82816-6 Typesetting SPiGlobal,Chennai,India PrintingandBinding Printedonacid-freepaper 10 9 8 7 6 5 4 3 2 1 v Contents Volume1 Preface xxiii AbouttheAuthor xxv AbouttheBook xxvii Acknowledgments xxix ListofAbbreviations xxxi 1 RearrangementReactions 1 Baeyer–VilligerOxidationorRearrangement 1 Mechanism 2 Application 2 ExperimentalProcedure(frompatentUS5142093A) 3 DakinOxidation(Reaction) 3 Mechanism 4 Application 4 ExperimentalProcedure(frompatentEP0591799B) 4 BambergerRearrangement 5 Mechanism 5 ExperimentalProcedure(frompatentCN102001954B) 6 BeckmannRearrangement 6 Mechanism 6 Application 7 ExperimentalProcedure(general) 7 PreparationofCaprolactam(frompatentUS3437655A) 7 BenzilicAcidRearrangement 8 Mechanism 9 Application 9 ExperimentalProcedure(frompatentUS20100249451B) 9 Baker–VenkataramanRearrangement 9 Mechanism 10 Application 10 ExperimentalProcedure(frompatentCN105985306B) 10 vi Contents ClaisenRearrangement 11 Mechanism 11 Application 12 ExperimentalProcedure(frompatentWO2016004632A1) 13 Eschenmoser–ClaisenRearrangement 13 Mechanism 13 Ireland–ClaisenRearrangement 14 Mechanism 14 Johnson–ClaisenRearrangement 15 Mechanism 15 OvermanRearrangement 15 Mechanism 16 CopeRearrangement 16 Mechanism 17 Application 17 ExperimentalProcedure(frompatentUS4421934A) 17 CurtiusRearrangement 17 Mechanism 18 Application 18 ExperimentalProcedure(frompatentEP2787002A1) 19 DemjanovRearrangement 19 Mechanism 20 Application 21 ExperimentalProcedure(fromReference[14],copyright2008, AmericanChemicalSociety) 21 Tiffeneau–DemjanovRearrangement 22 Mechanism 22 Application 23 ExperimentalProcedure(fromReference[10],copyright,TheRoyal SocietyofChemistry) 23 FriesRearrangement 23 Mechanism 24 Application 24 ExperimentalProcedure(frompatentUS9440940B2) 25 FavorskiiRearrangement 25 Mechanism 25 Application 26 ExperimentalProcedure(frompatentEP3248959A2) 26 Fischer–HeppRearrangement 26 Mechanism 27 ExperimentalProcedure(general) 27 HofmannRearrangement(Hofmanndegradationofamide) 28 Mechanism 28 Application 29 ExperimentalProcedure(frompatentCN105153023B) 29 Hofmann–MartiusRearrangement 29 Mechanism 30 Contents vii ExperimentalProcedure(frompatentDD295338A5) 30 LossenRearrangement 31 Mechanism 31 Application 32 ExperimentalProcedure(frompatentEP2615082B1) 32 OrtonRearrangement 32 Mechanism 33 Pinacol–PinacoloneRearrangement 33 Mechanism 34 Application 34 ExperimentalProcedure(general) 34 RupeRearrangement/Meyer–SchusterRearrangement 34 RupeRearrangement 35 Meyer–SchusterRearrangement 35 Mechanism 35 Application 36 ExperimentalProcedure(frompatentUS4088681A) 36 SchmidtRearrangementorSchmidtReaction 36 Mechanism 37 Application 37 ExperimentalProcedure(frompatentWO2009026444A1) 38 Wagner–MeerweinRearrangement 38 Mechanism 38 Application 39 WolffRearrangement 39 Mechanism 39 Alternatively 40 Application 40 ExperimentalProcedure(frompatentUS9175041B2) 9175041B2 40 Arndt–EistertHomologationorSynthesis 41 Mechanism 41 Application 42 ExperimentalProcedure(frompatentUS9399645B2) 42 Step1 42 Step2 42 ZininRearrangementorBenzidineandSemidineRearrangements 42 Mechanism 43 ExperimentalProcedure(frompatentUS20090069602A1) 44 References 45 Baeyer-VilligerOxidationorRearrangement 45 DakinOxidationorReaction 47 BambergerRearrangement 48 BeckmannRearrangement 48 BenzilicAcidRearrangement 50 Baker–VenkataramanRearrangement 51 viii Contents ClaisenRearrangement/Eschenmoser–Claisen Rearrangement/Ireland–ClaisenRearrangement/Johnson–Claisen Rearrangement/OvermanRearrangement 52 CopeRearrangement 53 CurtiusRearrangement 54 DemjanovRearrangement 56 Tiffeneau–DemjanovRearrangement 56 FriesRearrangement 56 FavorskiiRearrangement 58 Fischer–HeppRearrangement 58 HofmannRearrangement(HofmannDegradationofAmide) 59 Hofmann–MartiusRearrangement 60 LossenRearrangement 60 OrtonRearrangement 61 Pinacol–PinacoloneRearrangement 62 RupeRearrangement/Meyer–SchusterRearrangement 62 SchmidtRearrangementorSchmidtReaction 63 Wagner–MeerweinRearrangement 64 WolffRearrangement 65 Arndt–EistertHomologationorSynthesis 66 ZininRearrangementorBenzidineandSemidineRearrangements 67 2 CondensationReaction 69 AldolCondensationReaction 69 Application 70 ExperimentalProcedure(general) 71 EnantioselectiveAldolReaction(frompatentUS6919456B2) 71 MukaiyamaAldolReaction 72 Mechanism 72 Application 72 ExperimentalProcedure(frompatentDE102013011081A1) 73 EvansAldolReaction 73 Mechanism 74 Application 74 ExperimentalProcedure(frompatentWO2013151161A1) 74 HenryReaction 75 Mechanism 75 Application 76 ExperimentalProcedure(frompatentUS6919456B2) 76 PreparationofChiralCatalyst 76 Nitro-AldolReaction 76 BenzoinCondensation 76 Mechanism 77 Application 77 ExperimentalProcedure(frompatentDE3019500C2) 78 ClaisenCondensation 78 Mechanism 78 Contents ix Application 79 ExperimentalProcedure(frompatentUS9884836B2) 79 DarzensGlycidicEsterCondensation 80 Mechanism 80 Application 81 ExperimentalProcedure(frompatentJP2009512630A) 81 DieckmannCondensation 81 Mechanism 82 Application 82 ExperimentalProcedure(frompatentUS7132564B2) 82 KnoevenagelCondensation 83 Mechanism 83 Application 84 Lumefantrine 84 ExperimentalProcedure(frompatentWO2010136360A2) 84 PechmannCondensation(synthesisofcoumarin)(alsocalledvon Pechmanncondensation) 85 Mechanism 85 Application 86 ExperimentalProcedure(frompatentUS7202272B2) 86 PerkinCondensationorReaction 86 Mechanism 87 Application 88 ExperimentalProcedure(frompatentUS4933001A) 88 StobbeCondensation 88 Mechanism 89 Application 89 ExperimentalProcedure(frompatentUS20160137682A1) 90 References 90 AldolCondensationReaction 90 MukaiyamaAldolReaction 93 EvansAldolReaction 96 HenryReaction 98 BenzoinCondensation 99 ClaisenCondensation 101 DarzensGlycidicEsterCondensation 102 DieckmannCondensation 103 KnoevenagelCondensation 105 PechmannCondensation 106 PerkinCondensationorReaction 107 StobbeCondensation 108 3 Olefination,Metathesis,andEpoxidationReactions 111 Olefination 111 Corey–WinterOlefinSynthesis 111 Mechanism 112 Application 112 x Contents ExperimentalProcedure(frompatentUS5807866A) 112 Horner–Wadsworth–EmmonsReaction 113 Mechanism 113 Application 113 ExperimentalProcedure(frompatentJPWO2015046403A1) 114 Julia–LythgoeOlefination 114 Mechanism 115 ModifiedJuliaOlefination 115 Mechanism 115 Application 116 ExperimentalProcedure(frompatentCN103313983A) 116 Julia–KocienskiOlefination 117 Application 117 ExperimentalProcedure(frompatentWO2016125086A1) 118 KauffmannOlefination 118 Mechanism 119 Application 119 ExperimentalProcedure(frompatentWO2014183211A1) 119 PetersonOlefination 119 Mechanism 120 Application 121 ExperimentalProcedure(frompatentWO2017149091A1) 121 PetasisOlefination 122 Mechanism 122 Application 123 ExperimentalProcedure(frompatentUS5087790A) 123 TebbeOlefination 123 Mechanism 123 Application 124 ExperimentalProcedure(frompatentUS8809558B1) 124 WittigReactionorOlefination 124 Mechanism 125 Application 126 ExperimentalProcedure(frompatentWO2006045010A2) 126 Metathesis 127 OlefinMetathesis 127 Ring-ClosingMetathesis 127 Mechanism 128 ExperimentalProcedure(frompatent US20022018351A1) 128 CrossMetathesis 128 Ring-OpeningMetathesis 128 Ring-OpeningMetathesisPolymerization(ROMP) 129 AsymmetricEpoxidation 129 SharplessAsymmetricEpoxidation 129 Mechanism 129 Application 130
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