The chemistry of heterocycles : structure, reactions, synthesis and applications

648 Pages·2012·6.317 MB·English, German

by  Speicher, Andreas, Eicher, Theophil, Hauptmann, Siegfried

TheophilEicher,SiegfriedHauptmann,
andAndreasSpeicher
TheChemistryofHeterocycles
RelatedTitles
Majumdar,KrishnaC./Chattopadhyay, Larock,RichardC.
ShitalK.(eds.)
ComprehensiveOrganic
HeterocyclesinNaturalProduct Transformations,AGuideto
Synthesis FunctionalGroupPreparations,
TwoVolumeSet
2011
ISBN:978-3-527-32706-5
December2010
ISBN:978-1-118-03758-4
Alvarez-Builla,Julio/Vaquero,
JuanJose/Barluenga,Jose´(eds.)
Quin,LouisD./Tyrell,John
ModernHeterocyclicChemistry
Fundamentalsof Heterocyclic
2011 Chemistry
ISBN:978-3-527-33201-4
2010
ISBN:978-0-470-56669-5
Pozharskii,AlexanderF./Soldatenkov,
Anatoly/Katritzky,AlanR.
Joule,JohnA./Mills,Keith
HeterocyclesinLifeandSociety
HeterocyclicChemistry
AnIntroductiontoHeterocyclicChemistry,
BiochemistryandApplications
2010
2011 ISBN:978-1-4051-9365-8
ISBN:978-0-470-71410-2(Softcover)
ISBN:978-0-470-71411-9(Hardcover) Royer,Jacques(ed.)
AsymmetricSynthesisof
Li,JieJack
NitrogenHeterocycles
NameReactionsinHeterocyclic
ChemistryII 2009
ISBN:978-3-527-32036-3
2011
ISBN:978-0-470-08508-0 Petrov,ViacheslavA.
FluorinatedHeterocyclic
Cossy,Janine/Arseniyadis,Stellios/Meyer,
Compounds
Christophe(eds.)
MetathesisinNatural Product 2009
Synthesis ISBN:978-0-470-45211-0
2010
ISBN:978-3-527-32440-8
Theophil Eicher, Siegfried Hauptmann, and Andreas Speicher
The Chemistry of Heterocycles
Structure, Reactions, Synthesis, and Applications
Third, Completely Revised and Enlarged Edition
TheAuthors AllbookspublishedbyWiley-VCHare
carefullyproduced.Nevertheless,authors,
Prof.Dr.TheophilEicher editors,andpublisherdonotwarrantthe
SaarlandUniversity informationcontainedinthesebooks,
CampusB6.1 includingthisbook,tobefreeoferrors.
66123Saarbru¨cken Readersareadvisedtokeepinmindthat
statements,data,illustrations,procedural
detailsorotheritemsmayinadvertentlybe
inaccurate.
Prof.Dr.SiegfriedHauptmann†
LibraryofCongressCardNo.:appliedfor
Prof.Dr.AndreasSpeicher
SaarlandUniversity BritishLibraryCataloguing-in-Publication
FR8.1–OrganicChemistry Data
CampusC4.2 Acataloguerecordforthisbookisavailable
66123Saarbru¨cken fromtheBritishLibrary.
Bibliographicinformationpublishedby
theDeutscheNationalbibliothek
TheDeutscheNationalbibliothek
liststhispublicationintheDeutsche
Nationalbibliografie;detailedbibliographic
dataareavailableontheInternetat
<http://dnb.d-nb.de>.
©2012Wiley-VCHVerlag&Co.
KGaA,Boschstr.12,69469Weinheim,
Germany
Allrightsreserved(includingthoseof
translationintootherlanguages).Nopart
ofthisbookmaybereproducedinany
form–byphotoprinting,microfilm,orany
othermeans–nortransmittedortranslated
intoamachinelanguagewithoutwritten
permissionfromthepublishers.Registered
names,trademarks,etc.usedinthisbook,
evenwhennotspecificallymarkedassuch,
arenottobeconsideredunprotectedbylaw.
ISBNHardcover:978-3-527-32868-0
ISBNSoftcover:978-3-527-32747-8
CoverDesign Grafik-DesignSchulz,
Fußgo¨nheim
Typesetting LaserwordsPrivateLimited,
Chennai,India
PrintingandBinding MarkonoPrint
MediaPteLtd,Singapore
Printedonacid-freepaper
V
Contents
PrefacetotheThirdEdition IX
AbbreviationsandSymbols XI
1 TheStructureofHeterocyclicCompounds 1
Reference 4
2 SystematicNomenclatureofHeterocyclicCompounds 5
2.1 Hantzsch-WidmanNomenclature 6
2.2 ReplacementNomenclature 11
2.3 ExamplesofSystematicNomenclature 12
2.4 ImportantHeterocyclicSystems 15
3 Three-MemberedHeterocycles 17
3.1 Oxirane 17
3.2 Thiirane 26
3.3 2H-Azirine 29
3.4 Aziridine 32
3.5 Dioxirane 37
3.6 Oxaziridine 38
3.7 3H-Diazirine 40
3.8 Diaziridine 40
References 41
4 Four-MemberedHeterocyles 45
4.1 Oxetane 45
4.2 Thietane 49
4.3 Azete 50
4.4 Azetidine 51
4.5 1,2-Dioxetane 55
4.6 1,2-Dithiete 57
4.7 1,2-Dihydro-1,2-diazete 58
4.8 1,2-Diazetidine 58
References 59
VI Contents
5 Five-MemberedHeterocycles 61
5.1 Furan 61
5.2 Benzo[b]furan 80
5.3 Isobenzofuran 84
5.4 Dibenzofuran 86
5.5 Tetrahydrofuran 87
5.6 Thiophene 90
5.7 Benzo[b]thiophene 101
5.8 Benzo[c]thiophene 104
5.9 2,5-Dihydrothiophene 105
5.10 Thiolane 106
5.11 Selenophene 107
5.12 Pyrrole 108
5.13 Indole 125
5.14 Carbazole 148
5.15 Isoindole 150
5.16 Indolizine 152
5.17 Pyrrolidine 157
5.18 Phosphole 161
5.19 1,3-Dioxolane 162
5.20 1,2-Dithiole 163
5.21 1,2-Dithiolane 164
5.22 1,3-Dithiole 165
5.23 1,3-Dithiolane 165
5.24 Oxazole 166
5.25 Benzoxazole 177
5.26 4,5-Dihydrooxazole 181
5.27 Isoxazole 185
5.28 4,5-Dihydroisoxazole 193
5.29 2,3-Dihydroisoxazole 198
5.30 Thiazole 199
5.31 Benzothiazole 208
5.32 Penam 212
5.33 Isothiazole 214
5.34 Imidazole 217
5.35 Benzimidazole 229
5.36 Imidazolidine 234
5.37 Pyrazole 236
5.38 Indazole 243
5.39 4,5-Dihydropyrazole 246
5.40 Pyrazolidine 249
5.41 1,2,3-,1,2,4-,1,3,4-Oxadiazole 249
5.42 1,2,5-Oxadiazole 251
5.43 1,2,3-Thiadiazole 254
5.44 1,2,4-Thiadiazole 256
Contents VII
5.45 1,2,3-Triazole 258
5.46 Benzotriazole 265
5.47 1,2,4-Triazole 268
5.48 Tetrazole 273
References 280
6 Six-MemberedHeterocycles 297
6.1 PyryliumIon 297
6.2 2H-Pyran 305
6.3 2H-Pyran-2-one 306
6.4 3,4-Dihydro-2H-pyran 313
6.5 Tetrahydropyran 317
6.6 2H-Chromene 319
6.7 2H-Chromen-2-one 321
6.8 1-BenzopyryliumIon 327
6.9 4H-Pyran 329
6.10 4H-Pyran-4-one 331
6.11 4H-Chromene 335
6.12 4H-Chromen-4-one 336
6.13 Chroman 341
6.14 Pyridine 345
6.15 Pyridones 381
6.16 Quinoline 386
6.17 Isoquinoline 406
6.18 QuinoliziniumIon 420
6.19 Dibenzopyridines 423
6.20 Piperidine 429
6.21 Phosphabenzene 434
6.22 1,4-Dioxin,1,4-Dithiin,1,4-Oxathiin 438
6.23 1,4-Dioxane 440
6.24 Oxazines 442
6.25 Morpholine 447
6.26 1,3-Dioxane 449
6.27 1,3-Dithiane 453
6.28 Cepham 455
6.29 Pyridazine 458
6.30 Pyrimidine 463
6.31 Purine 474
6.32 Pyrazine 481
6.33 Piperazine 486
6.34 Pteridine 487
6.35 Benzodiazines 491
6.36 1,2,3-Triazine 501
6.37 1,2,4-Triazine 504
6.38 1,3,5-Triazine 508
VIII Contents
6.39 1,2,4,5-Tetrazine 512
References 517
7 Seven-MemberedHeterocycles 529
7.1 Oxepin 529
7.2 Thiepin 532
7.3 Azepine 533
7.4 Diazepines 540
References 545
8 LargerRingHeterocycles 547
8.1 Azocine 547
8.2 HeteroninesandLarger-MemberedHeterocycles 549
8.3 Tetrapyrroles 551
References 558
9 ProblemsandTheirSolutions 561
References 614
Indices 621