Keywords:
Heterocyclic compounds.
;
Electronic books.
Type of Medium:
Online Resource
Pages:
1 online resource (575 pages)
Edition:
1st ed.
ISBN:
9780471461432
Series Statement:
Chemistry of Heterocyclic Compounds: a Series of Monographs ; v.58
URL:
https://ebookcentral.proquest.com/lib/geomar/detail.action?docID=469254
Language:
English
Note:
Intro -- THE PYRAZINES Supplement I -- The Chemistry of Heterocyclic Compounds Introduction to the Series -- Preface -- Contents -- CHAPTER 1 PRIMARY SYNTHESES FROM ALIPHATIC OR CARBOCYCLIC SYNTHONS -- 1.1 From a Single Six-Atom Synthon -- 1.1.1 By Completion of the N-C2 Bond -- 1.1.1.1 From Appropriate w-Unsaturated Azaalkylamines -- 1.1.1.2 From Appropriate w-Halogeno(azaalkylamines) -- 1.1.1.3 From Appropriate a,w-Diamino(azaalkanes) -- 1.1.1.4 From Appropriate w-Amino(azaalkanols) -- 1.1.1.5 From Appropriate w-Amino(azaalkanals) -- 1.1.1.6 From Appropriate w-Amino(azaalkanones) -- 1.1.1.7 From Appropriate w-Amino(azaalkanoic Acids) -- 1.1.1.8 From Appropriate w-Amino(azaalkanoic Esters) -- 1.1.1.9 From Appropriate w-Amino(azaalkanamides) -- 1.1.1.10 From Appropriate w-Amino(azaalkanenitriles) -- 1.1.2 By Completion of the C2-C3 Bond -- 1.2 From Two Synthons -- 1.2.1 By Using a One-Atom and a Five-Atom Synthon -- 1.2.1.1 Where the One-Atom Synthon Supplies N1 -- 1.2.1.2 Where the One-Atom Synthon Supplies C2 -- 1.2.2 By Using a Two-Atom and a Four-Atom Synthon -- 1.2.2.1 Where the Two-Atom Synthon Supplies N1 + C2 -- 1.2.2.2 Where the Two-Atom Synthon Supplies C2 + C3 -- 1.2.3 By Using Two Three-Atom Synthons -- 1.2.3.1 Where Identical Synthons Provide N1 + C2 + C3 and N4 + C5 + C6 -- 1.2.3.2 Where Different Synthons Provide N1 + C2 + C3 and N4 + C5 + C6 -- 1.2.3.3 Where the Synthons Provide N1 + C2 + C6 and C3 + N4 + C5 -- 1.3 From Three Synthons -- 1.4 From Four or More Synthons -- 1.4.1 Where Synthons Provide N1, C2 + C3, N4, C5 + C6 -- 1.4.2 Where Synthons Provide N1 + C2, C3 + N4, C5, C6 -- 1.4.3 Where Synthons Provide N1 + C2, C3, N4 + C5, C6 -- 1.5 Appendix: Glance Index to Typical Pyrazine Derivatives Available from Aliphatic or Carbocyclic Synthons -- CHAPTER 2 PRIMARY SYNTHESES FROM OTHER HETEROCYCLIC SYSTEMS.
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2.1 Pyrazines from Other Heteromonocyclic Systems -- 2.1.1 Azepines as Substrates -- 2.1.2 Azetes as Substrates -- 2.1.3 Azirines as Substrates -- 2.1.4 Azocines as Substrates -- 2.1.5 1,2-Diazepines as Substrates -- 2.1.6 1,4-Diazepines as Substrates -- 2.1.7 Furans as Substrates -- 2.1.8 Imidazoles as Substrates -- 2.1.9 Isoxazoles as Substrates -- 2.1.10 Oxazoles as Substrates -- 2.1.11 Oxirenes as Substrates -- 2.1.12 Pyridazines as Substrates -- 2.1.13 Pyridines as Substrates -- 2.1.14 Pyrroles as Substrates -- 2.1.15 1,2,5-Selenadiazoles as Substrates -- 2.1.16 1,2,5-Thiadiazoles as Substrates -- 2.1.17 Thiirenes as Substrates -- 2.2 Pyrazines from Heterobicyclic Systems -- 2.2.1 1, 2-Diazabicyclo[2.2.0]hexanes as Substrates -- 2.2.2 2,4,-Diazabicyclo[3.1.0]hexanes as Substrates -- 2.2.3 2,3-Dioxa-5,7-diazabicyclo-[2.2.2]octanes as Substrates -- 2.2.4 Furo[2,3-b]pyrazines as Substrates -- 2.2.5 Imidazo[1,2-a]pyrazines as Substrates -- 2.2.6 Indoles as Substrates -- 2.2.7 Isoxazolo[2,3-a]pyrazines as Substrates -- 2.2.8 Isoxazolo[4,5-b]pyrazines as Substrates -- 2.2.9 Pteridines as Substrates -- 2.2.10 Pyrazino[2,3-d][1,3]oxazines as Substrates -- 2.2.11 Pyrazino[2,3-e][1,3,4]thiadiazines as Substrates -- 2.2.12 Quinoxalines as Substrates -- 2.2.13 4-Thia-1-azabicyclo[3.2.0]heptanes as Substrates -- 2.2.14 [1,2,5]Thiadiazolo[3,4-b]pyrazines as Substrates -- 2.2.15 Thiazolo[3,2-a]pyrazines as Substrates -- 2.2.16 Thiazolo[3,4-a]pyrazines as Substrates -- 2.3 Pyrazines from Heterotricyclic Systems -- 2.4 Pyrazines from Spiro Heterocycles -- 2.5 Appendix: Glance Index to Typical Pyrazine Derivatives Available from Other Heterocyclic Systems -- CHAPTER 3 PYRAZINE, ALKYLPYRAZINES, AND ARYLPYRAZINES -- 3.1 Pyrazine -- 3.1.1 Preparation of Pyrazine -- 3.1.2 Properties of Pyrazine -- 3.1.3 Reactions of Pyrazine -- 3.2 C-Alkyl- and C-Arylpyrazines.
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3.2.1 Preparation of C-Alkyl- and C-Arylpyrazines -- 3.2.1.1 By Direct C-Alkylation -- 3.2.1.1.1 General Procedures for C-Alkylation -- 3.2.1.1.2 C-Alkylation in the Schöllkopf Synthesis -- 3.2.1.2 By Replacement of Halogeno Substituents -- 3.2.1.3 By Replacement of Alkoxy, Cyano, Nitro, or Oxo Substituents -- 3.2.1.4 By Interconversion of Simple Alkyl Substituents -- 3.2.1.5 By Elimination of Functionality from Existing Substituents -- 3.2.1.6 By Ipso-Substitution of Trimethylsiloxycarbonyl Substituents -- 3.2.2 Preparation of N-Alkyl- and N-Arylpiperazines -- 3.2.2.1 By N-Alkylation Processes -- 3.2.2.2 By Reduction of N-Acyl or N-Alkoxycarbonylpiperazines -- 3.2.2.3 By Miscellaneous Routes -- 3.2.3 Properties of Alkyl- and Arylpyrazines -- 3.2.4 Reactions of Alkyl- and Arylpyrazines -- 3.2.4.1 Oxidative Reactions -- 3.2.4.2 Reductive Reactions -- 3.2.4.3 Extranuclear Halogenation -- 3.2.4.4 Extranuclear Alkylation -- 3.2.4.5 Extranuclear Alkylidenation -- 3.2.4.6 Extranuclear Acylation or Carboxylation -- 3.2.4.7 Cyclization -- 3.2.4.8 "Ammoxidation" of Methyl to Cyano Groups -- 3.2.4.9 Addition Reactions at Alkenyl or Alkynyl Substituents -- 3.2.4.10 Miscellaneous Reactions -- 3.3 N-Alkylpyrazinium Salts and Related Ylides -- 3.3.1 Preparation of N-Alkylpyrazinium Salts -- 3.3.2 Reactions of N-Alkylpyrazinium Salts -- CHAPTER 4 HALOGENOPYRAZINES -- 4.1 Preparation of Nuclear Halogenopyrazines -- 4.1.1 Nuclear Halogenopyrazines from Pyrazinones -- 4.1.2 Nuclear Halogenopyrazines by Direct Halogenation -- 4.1.3 Nuclear Halogenopyrazines by Deoxidative Halogenation of Pyrazine N-Oxides -- 4.1.4 Nuclear Halogenopyrazines from Pyrazinamines -- 4.1.5 Nuclear Halogenopyrazines by Transhalogenation -- 4.1.6 Nuclear Halogenopyrazines via Trimethylsiloxypyrazines -- 4.2 Reactions of Nuclear Halogenopyrazines -- 4.2.1 Aminolysis of Nuclear Halogenopyrazines.
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4.2.2 Hydrolysis of Nuclear Halogenopyrazines -- 4.2.3 Alcoholysis or Phenolysis of Nuclear Halogenopyrazines -- 4.2.4 Thiolysis of Nuclear Halogenopyrazines -- 4.2.5 Alkanethiolysis or Arenethiolysis of Nuclear Halogenopyrazines -- 4.2.6 Azidolysis of Nuclear Halogenopyrazines -- 4.2.7 Hydrogenolysis of Nuclear Halogenopyrazines -- 4.2.8 Cyanolysis of Nuclear Halogenopyrazines -- 4.2.9 Miscellaneous Displacement Reactions of Nuclear Halogenopyrazines -- 4.2.10 Fission, Rearrangement, or Cyclocondensation of Nuclear Halogenopyrazines -- 4.3 Preparation of Extranuclear Halogenopyrazines -- 4.3.1 Extranuclear Halogenopyrazines from Corresponding Hydroxypyrazines -- 4.3.2 Extranuclear Halogenopyrazines by Minor Procedures -- 4.4 Reactions of Extranuclear Halogenopyrazines -- CHAPTER 5 OXYPYRAZINES -- 5.1 Tautomeric Pyrazinones -- 5.1.1 Preparation of Tautomeric Pyrazinones -- 5.1.2 Reactions of Tautomeric Pyrazinones -- 5.1.2.1 Conversion into Pyrazinethiones -- 5.1.2.2 Conversion into O- and/or N- Alkylated Derivatives -- 5.1.2.3 Conversion into O- and/or N-Acylated Derivatives -- 5.1.2.4 Miscellaneous Reactions -- 5.2 Extranuclear Hydroxypyrazines -- 5.2.1 Preparation of Extranuclear Hydroxypyrazines -- 5.2.2 Reactions of Extranuclear Hydroxypyrazines -- 5.3 Nuclear and Extranuclear Alkoxy- or Aryloxypyrazines -- 5.3.1 Preparation of Alkoxy- or Aryloxypyrazines -- 5.3.2 Reactions of Alkoxy- or Aryloxypyrazines -- 5.4 Nontautomeric Pyrazinones and N-Alkylpyraziniumolates -- 5.4.1 Preparation of Nontautomeric Pyrazinones -- 5.4.2 Reactions of Nontautomeric Pyrazinones -- 5.5 Pyrazine N-Oxides -- 5.5.1 Preparation of Pyrazine N-Oxides -- 5.5.1.1 From N-Alkoxypyrazinones -- 5.5.1.2 By Direct N-Oxidation -- 5.5.2 Reactions of Pyrazine N-Oxides -- 5.5.2.1 Deoxygenation -- 5.5.2.2 O-Alkylation or O-Acylation -- 5.5.2.3 Conversion into C-Acyloxypyrazines.
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5.5.2.4 Conversion into C-Amino-, C-Azido-, C-Cyano-, or C-Alkylthiopyrazines -- 5.5.2.5 Miscellaneous Reactions -- 5.6 Appendix: Trivial Names for Pyrazine Derivatives -- CHAPTER 6 THIOPYRAZINES -- 6.1 Pyrazinethiones and Pyrazinethiols -- 6.1.1 Preparation of Pyrazinethiones and Pyrazinethiols -- 6.1.2 Reactions of Pyrazinethiones and Pyrazinethiols -- 6.2 Alkylthiopyrazines and Dipyrazinyl Sulfides -- 6.2.1 Preparation of Alkylthiopyrazines -- 6.2.2 Reactions of Alkylthiopyrazines -- 6.2.2.1 Oxidation to Sulfoxides or Sulfones -- 6.2.2.2 Miscellaneous Reactions -- 6.3 Dipyrazinyl Disulfides and Pyrazinesulfonic Acid Derivatives -- 6.4 Pyrazine Sulfoxides and Sulfones -- CHAPTER 7 NITRO-, AMINO-, AND RELATED PYRAZINES -- 7.1 Nitropyrazines -- 7.1.1 Preparation of Nitropyrazines -- 7.1.2 Reactions of Nitropyrazines -- 7.2 Nitrosopyrazines -- 7.2.1 C-Nitrosopyrazines -- 7.2.2 N-Nitrosopiperazines and Related Compounds -- 7.3 Regular Aminopyrazines -- 7.3.1 Preparation of Regular Aminopyrazines -- 7.3.2 Reactions of Regular Aminopyrazines -- 7.3.2.1 N-Acylation of Aminopyrazines and Subsequent Cyclizations -- 7.3.2.2 N-Alkylidenation of Aminopyrazines and Subsequent Cyclizations -- 7.3.2.3 N-Alkylation of Aminopyrazines and Subsequent Cyclizations -- 7.3.2.4 Conversion into Ureidopyrazines or Related Products -- 7.3.2.5 Conversion into Trialkylsilylamino-, Triphenylphosphoranylideneamino-, or Dimethylsulfimidopyrazines -- 7.3.2.6 Miscellaneous Minor Reactions -- 7.4 Preparation and Reactions of Hydrazinopyrazines -- 7.5 Preparation, Structure, and Reactions of Azidopyrazines -- 7.6 Nontautomeric Iminopyrazines -- 7.7 Arylazopyrazines -- CHAPTER 8 PYRAZINECARBOXYLIC ACIDS AND RELATED DERIVATIVES -- 8.1 Pyrazinecarboxylic Acids -- 8.1.1 Preparation of Pyrazinecarboxylic Acids -- 8.1.2 Reactions of Pyrazinecarboxylic Acids.
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8.2 Pyrazinecarboxylic Esters.
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