Chemistry of Heterocyclic Compounds. Volume 2. Six-Membered Heterocyclic Nitrogen Compounds With Four Condensed Rings

Interscirnce Publishers, Inc., 1951. — 345 p. The Chemistry of Heterocyclic Compounds has been published since 1950 under the initial editorship of Arnold Weissberger, and later, until his death in 1984, under the joint editorship of Arnold Weissberger and Edward C. Taylor. In 1997, Peter Wipf joined Prof. Taylor as editor. This series attempts to make the extraordinarily complex and diverse field of heterocyclic chemistry as organized and readily accessible as possible. Each volume has traditionally dealt with syntheses, reactions, properties, structure, physical chemistry, and utility of compounds belonging to a specific ring system or class (e.g., pyridines, thiophenes, pyrimidines, threemembered ring systems). This series has become the basic reference collection for information on heterocyclic compounds. Contents Preface Introduction Aznaphtacenes Monoazanaphthacenes 1-Aznaphtacene 2-Aznaphtacene 5-Aznaphtacene Diazanaphthacenes 1,3-Diazanaphthacene 1,4-Diazanaphthacene 1,1-Diazanaphthacene 2,3-Diazanaphthacene 5,6-Diazanaphthacene 5,11-Diazanaphthacene 5,12-Diazanaphthacene Triazanaphthacenes 1,6,11-Triazanaphthacene 5,6,11-Triazanaphthacene Tetrazanaphthacenes 1,3,5,12-Tetrazanaphthacene 5,6,11, 12.Tetrazanaphthacene 1,4,6,11-Tetrazanaphthacene Azabenz[a]anthracenes Monozabenz[a]anthracenes 1-Azabenz[a]anthracene 4-Azabenz[a]anthracene Alkyl Derivatives Oxidation Products Halogen Derivatives Nitro Derivatives Sulfonated and Hydroxylated Derivatives Physical Properties Amino Compounds 5-Azabenz[a]anthracene 8-Azabenz[a]anthracene 10-Azabenz[a]anthracene 11-Azabenz[a]anthracene Diazabenz[a]anthracenes 1,3-Diazabenz[alanthracene 1,4-Diazabenz[a]anthracene 1,7-Diazabenz[a]anthracene 1,12-Diazabenz[a]anthracene 2,4-Diazabenz[a]anthracene 4,7-Diazabenz[a]anthracene 4,12-Diazabenz[a]anthracene 5,7-Diazabenz[a]anthracene Ciba Yellow 3C Hochst Yellow U Hochst Yellow R 5,12-Diazabenz[a]anthracene 6,7-Diazabenz[a]anthracene 6,12-Diazabenz[a]anthracene Triazabenz[a]anthracenes Tetrazabenz[a]anthracenes Pentatabenz[a]anthracenes 4,7,12-Triazabenz[a]anthracene 6,7,12-Triazabenz[a]anthracene 7,8,10,12-Tetrazabenz[a]anthracene 7,9,11,12-Tetrazabenz[a]anthracene 4,7,9,11,12-Pentazabenz[a]anthracene 4,7,8,10,12-Pentazabenz[a]anthracene Azabenzo[c]phenanthrenes Monoazabenzo[c]phenanthrenes 1-Azabenzo[c]phenanthrene 2-Azabenzo[c]phenanthrene 4-Azabenzo[c]phenanthrene 6-Azabenzo[c]phenanthrene Diazabenzo[c]phenanthrenes 1,3-Diazabenzo[c]phenanthrene 5,8-Diazabenzo[c]phenanthrene Azachrysenes Monoazachrysen 1-Azachrysene 2-Azachrysene 3-Azachrysene 5-Azachryscne Chelidonine Sanguinarine a-Homochelidonine Chelerythrine 6-Azachryscne Diazachrysencs 4.10-Diazachrysene Azatriphenylenes Monoazatriphenylenes 1-Azatriphenylene 2-Azatriphenylene Diazatriphenylenes 1,2-Diazatriphenylene 1,4-Diazatriphenylene 2,3-Diazatriphenylcne 1,8-Diazatriphenylene 2,3-Diazatriphenylene Triazatriphenylencs 1,2,4-Triazatriphenylene 1,5,9-Triazatriphenylene Azabenzanthrenes Introduction Historical Nomenclature Numbering 3-Azabenzanthrones (Anthrapyridines. Anthrapyridones) 1,3-Diazabcnzanthrones (Anthrapyrimidines) Monoazabenzanthrenes 7H,1-Azabenzanthrene Preparation Reactions Properties 2-Atabenzanthrene Preparation Reactions Properties 3-Azabenzanthrenes Monoketo Derivatives: 3-Azabenzanthrones (Anthrapyridines) Diketo Derivatives: 2-Keto-3-azabenzanthrones (Anthrapyridons) Ring Closure, from 1-Aminoanthraquinone Ring Closure. Seka’s Method In the 1-Position Inthe 3-Pdtion In the CPOeition In the &Position In the 8- and 11-Positions Mtecllaneous Formation of Substituted 2-Keto-3-azanthrones Products of Uncertain Structures Wianthrapyridones 5-Azabenzanthrenes 6-Azabenzanthrenes Introduction Histotical Nomenclature Stereochemistry Prepatation Reactions Properties Source,Properties and Physiological Action of the Natural Alkaloids Apomorphine Apocodeine Morphothebaine Tuduranine Isothebaine Laurcline Laurotetanine Actinodaphnine Boldine Corytuberine Laurepukine N-Methyllaurotetanine d-Corydin Isocorydine Domesticine Bulbocapnine Glaucine Epidicentrine Dicentrine 7H,8-Azabenzanthrene 7H,11-Azabenzanthrene Preparation Reactions Properties x-Azabcnzanthrenes Diazabenzanthrene 1,2-Diazabenzanthrones (Pyridazinoanthrones) Historical 3-Subetituted 1,2-Diazabenzanthrones Preparation Properties Uses 3-Keto-1,2-diazabenzanthrone Preparation Properties Uses Monoketo-1, 3-diazabenzanthrenes (Anthrapyrimidines) Ring Closure Replacement Reactions Amines Halogenated Derivatives Sulfonic Acids Hydroxy Derivatives Miscellaneous Derivatives Acylamino-1,3-diazabenzanthrones Arylamino-1,3-diazabenzanthrones Haloamino-1,3-diazabenzanthrones N-Akylsulfonic Acids Nitriles Carboxylic Acids Oxy, Thio, and Seleno Derivatives Diketo-1,3-diazabenzanthrenes (Anthrapyrimidones) Products of Uncertain Structure Physical Properties Uses Azapyrenes Monoazapyrenes 2-Azapyrene 4-Azapyrene Diazapyrenes 2,7-Diazapyrene 4,9-Diazapyrene Tetrazapyrene 1,3,6,8-Tetrazapyrene Azabenzanthrenes: Addendum 2-Keto-3-methyl-3-azabenzanthrones 1,3-Diazabenzanthrone Aryl Group in the 4 Position Sulfobenzoylation Index Interscirnce Publishers, Inc., 1951. — 345 p.The __Chemistry of Heterocyclic Compounds__ has been published since 1950 under the initial editorship of Arnold Weissberger, and later, until his death in 1984, under the joint editorship of Arnold Weissberger and Edward C. Taylor. In 1997, Peter Wipf joined Prof. Taylor as editor. This series attempts to make the extraordinarily complex and diverse field of heterocyclic chemistry as organized and readily accessible as possible. Each volume has traditionally dealt with syntheses, reactions, properties, structure, physical chemistry, and utility of compounds belonging to a specific ring system or class (e.g., pyridines, thiophenes, pyrimidines, threemembered ring systems). This series has become the basic reference collection for information on heterocyclic compounds. **Contents** PrefaceIntroduction **Aznaphtacenes** Monoazanaphthacenes1-Aznaphtacene2-Aznaphtacene5-AznaphtaceneDiazanaphthacenes1,3-Diazanaphthacene1,4-Diazanaphthacene1,1-Diazanaphthacene2,3-Diazanaphthacene5,6-Diazanaphthacene5,11-Diazanaphthacene5,12-DiazanaphthaceneTriazanaphthacenes1,6,11-Triazanaphthacene5,6,11-TriazanaphthaceneTetrazanaphthacenes1,3,5,12-Tetrazanaphthacene5,6,11,12.Tetrazanaphthacene1,4,6,11-Tetrazanaphthacene **Azabenz[a]anthracenes** Monozabenz[a]anthracenes1-Azabenz[a]anthracene4-Azabenz[a]anthraceneAlkyl DerivativesOxidation ProductsHalogen DerivativesNitro DerivativesSulfonated and Hydroxylated DerivativesPhysical PropertiesAmino Compounds5-Azabenz[a]anthracene8-Azabenz[a]anthracene10-Azabenz[a]anthracene11-Azabenz[a]anthraceneDiazabenz[a]anthracenes1,3-Diazabenz[alanthracene1,4-Diazabenz[a]anthracene1,7-Diazabenz[a]anthracene 1,12-Diazabenz[a]anthracene2,4-Diazabenz[a]anthracene4,7-Diazabenz[a]anthracene4,12-Diazabenz[a]anthracene5,7-Diazabenz[a]anthraceneCiba Yellow 3CHochst Yellow UHochst Yellow R5,12-Diazabenz[a]anthracene6,7-Diazabenz[a]anthracene 6,12-Diazabenz[a]anthraceneTriazabenz[a]anthracenesTetrazabenz[a]anthracenesPentatabenz[a]anthracenes4,7,12-Triazabenz[a]anthracene6,7,12-Triazabenz[a]anthracene7,8,10,12-Tetrazabenz[a]anthracene7,9,11,12-Tetrazabenz[a]anthracene4,7,9,11,12-Pentazabenz[a]anthracene 4,7,8,10,12-Pentazabenz[a]anthracene **Azabenzo[c]phenanthrenes** Monoazabenzo[c]phenanthrenes1-Azabenzo[c]phenanthrene2-Azabenzo[c]phenanthrene4-Azabenzo[c]phenanthrene6-Azabenzo[c]phenanthreneDiazabenzo[c]phenanthrenes1,3-Diazabenzo[c]phenanthrene5,8-Diazabenzo[c]phenanthrene **Azachrysenes** Monoazachrysen 1-Azachrysene2-Azachrysene3-Azachrysene5-AzachryscneChelidonineSanguinarinea-HomochelidonineChelerythrine6-AzachryscneDiazachrysencs4.10-Diazachrysene **Azatriphenylenes** Monoazatriphenylenes1-Azatriphenylene2-AzatriphenyleneDiazatriphenylenes1,2-Diazatriphenylene1,4-Diazatriphenylene2,3-Diazatriphenylcne1,8-Diazatriphenylene2,3-DiazatriphenyleneTriazatriphenylencs1,2,4-Triazatriphenylene1,5,9-Triazatriphenylene **Azabenzanthrenes** IntroductionHistoricalNomenclatureNumbering3-Azabenzanthrones (Anthrapyridines. Anthrapyridones)1,3-Diazabcnzanthrones (Anthrapyrimidines)Monoazabenzanthrenes7H,1-AzabenzanthrenePreparationReactionsProperties2-AtabenzanthrenePreparationReactionsProperties3-Azabenzanthrenes Monoketo Derivatives: 3-Azabenzanthrones (Anthrapyridines)Diketo Derivatives: 2-Keto-3-azabenzanthrones (Anthrapyridons)Ring Closure, from 1-AminoanthraquinoneRing Closure. Seka’s MethodIn the 1-PositionInthe 3-PdtionIn the CPOeitionIn the &PositionIn the 8- and 11-PositionsMtecllaneousFormation of Substituted 2-Keto-3-azanthronesProducts of Uncertain StructuresWianthrapyridones5-Azabenzanthrenes6-AzabenzanthrenesIntroductionHistoticalNomenclatureStereochemistryPrepatationReactionsPropertiesSource,Properties and Physiological Action of the Natural AlkaloidsApomorphineApocodeineMorphothebaineTuduranineIsothebaineLaurclineLaurotetanineActinodaphnineBoldineCorytuberineLaurepukineN-Methyllaurotetanined-CorydinIsocorydineDomesticineBulbocapnineGlaucineEpidicentrineDicentrine7H,8-Azabenzanthrene 7H,11-Azabenzanthrene PreparationReactionsPropertiesx-AzabcnzanthrenesDiazabenzanthrene1,2-Diazabenzanthrones (Pyridazinoanthrones)Historical3-Subetituted 1,2-DiazabenzanthronesPreparationPropertiesUses3-Keto-1,2-diazabenzanthronePreparationPropertiesUsesMonoketo-1, 3-diazabenzanthrenes (Anthrapyrimidines)Ring ClosureReplacement ReactionsAminesHalogenated DerivativesSulfonic AcidsHydroxy DerivativesMiscellaneous DerivativesAcylamino-1,3-diazabenzanthronesArylamino-1,3-diazabenzanthronesHaloamino-1,3-diazabenzanthronesN-Akylsulfonic AcidsNitrilesCarboxylic AcidsOxy, Thio, and Seleno DerivativesDiketo-1,3-diazabenzanthrenes (Anthrapyrimidones)Products of Uncertain StructurePhysical PropertiesUses **Azapyrenes** Monoazapyrenes2-Azapyrene4-AzapyreneDiazapyrenes2,7-Diazapyrene4,9-DiazapyreneTetrazapyrene1,3,6,8-Tetrazapyrene **Azabenzanthrenes: Addendum** 2-Keto-3-methyl-3-azabenzanthrones1,3-DiazabenzanthroneAryl Group in the 4 PositionSulfobenzoylationIndex