Condensed Pyridazine and Pyrazine Rings, Volume 5

J. C. Simpson, Late Member of Scientific Staff, Medical Research Council, England.

• Preface ixPart I. CinnolinesI. General Introduction to Cinnoline Derivatives. Preparation and Properties of Cinnoline 31. General Introduction to Cinnoline Derivatives 32. Preparation and Properties of Cinnoline 4II. 4-Aryl-, 4-Acyl-, and 4-Carboxycinnolines 61. 4-Arylcinnolines 62. 4-Acylcinnolines 113. 4-Carboxycinnolines (Cinnoline-4-carboxylic Acids) 11III. 4-Methylcinnolines 13IV. 4-Hydroxycinnolines 161. Methods of Preparation 16A. Richter Synthesis 16B. Pfannstiel and Janecke Synthesis 17C. Borsche Synthesis 172. Properties 23A. 4-Hydroxycinnolines Other Than 4-IIydroxycinnoiine-3-carboxylic Acids 23B. 4-Hydroxycinnoline-3-carboxylic Acids 24V. 4-Chloro-, 4-Alkoxy-, and 4-Phenoxycinnolines 291. 4-ChlorocinnoIines 292. 4-Alkoxycinnolines 313. 4-Phenoxvcinnolines 32VI. 4-Aminocinnolines 351. Primary Amino Compounds 352. Secondary Amino Compounds 36A. 4-Arylaminocinnolines 36B. 4-Dialkylaminoalkylaminocinnolines 36C. 4-Hydroxylamino-7-acetylcinnolineoxime 38VII. Cinnoline Quaternary Salts 39A. Preparation 39B. Structure 39C. Reactions 43VIII. Reduced Cinnolines 461. Reduced Cinnolines with Nonoxvgenated Rings 46A. Dihydrocinnolines 46B. Tetrahydrocinnolines 47C. Hexahydrocinnolines 482. Reduced Cinnolines with Oxygenated Rings 48A. Reduced 3- and 4-Hydroxycinnolines 48B. l-Methyl-4-keto-l,4-dihydrocinnolines 48C. Methyl 4-Keto-4,6-dihydrocinnolyl-6-nitronates 49D. 3-Acetoxy-2-aryl-6-keto-2,6-dihydrocinnolines 49E. 2-Pbenyl-3-keto-4-hydroxy-2,3,5,6,7,8-hexahydrocinnoline 51IX. Cinnolines Containing Additional Fused Rings 521. 3,4-Benzocinnolines 522. Tetrahydro-3,4-benzocinnolines 573. Other Cinnolines with Additional Aromatic Rings 574. Cinnolines Containing Bridged Rings 615. Cinnolines Containing Fused Heterocyclic Rings 62Part II. PhthalazinesX. Phthalazines Unsubstituted in the Hetero Ring 691. Phthalazine 692. 5,6-Dihydroxy phthalazine 71XI. 1-Alkyi-, 1-Aryl-, and 1,4-Diaryiphthalazlnes 721. 1-AIkyl- and 1-Arvlphthalazines 722. 1,4-Diarylphthalazines 76XII. 1-Hydroxyphthalazines 78A. Preparation 78B. Properties 78XIII. Alkyl, Aryl, and Acyl Derivatives of 4-(l-)Hydroxyphthalazines 841. O-Derivatives 842. N-Derivatives (3-Substituted-4-keto-3,4-dihydrophthalazines)... 85A. Compounds without a l-Substituent; 3-Aryl-, 3-Alkyl-, and 3-Aralkyl-4-keto-3,4-dihydrophthalazines 85B. Compounds with a l-Substituent 953. Derivatives of Unknown Structure 96XIV. l-Hydroxy-3-aryl-3,4-dihydrophthalazine-4-acetic Acids 106A. Preparation 106B. Properties 108XV. 3-Aryl-l-ketophthalazines 119A. Preparation 119B. Properties and Reactions 126XVI. Methylated Derivatives of 3-Aryl-l-ketophthalazines 1301. Derivatives of Compounds Containing a Hydrogen Atom at C4 130A. l-Methoxy-4-alkoxy-3-aryl-3,4-dihydrophthalazines 130B. l-Methoxy-3-arylphthalazinium Perchlorates 1332. Derivatives of Compounds Containing a Methyl Group at C(:l-Methoxy-3-aryI-4-methylene-3,4-dihydrophthalazines 133XVII. 1,4-Dlhydroxyphthalazines 140A. Preparation 140B. Properties 143C. Chemiluminescence of Phthalazine Derivatives 153XVIII. Monoalkyl and Monoacyl Derivatives of 1,4-Dihydroxyphthal-azines 1571. O-Derivatives 1572. .V-Derivatives (l-Hydroxy-3-substituted-4-keto-3,4-dihydro-phthalazines) 158A. Compounds Containing No Substituent in the Benzene Ring 158B. Compounds Containing a Substituent in the Benzene Ring 1623. Derivatives of Unknown Structure 165XIX. Dialkyl and Diacyl Derivatives of 1,4-Dihydroxyphthalazines 1681. 1,4-Derivatives 1682. 1,3-Derivatives (1-Alkoxy- and l-Acetoxy-3-substituted-4-keto-3,4-dihydrophthalazines) 169A. Preparation 169B. Properties 170C. Structure of Alkoxy Compounds 1733. 2,3-Derivatives 1754. Derivatives of Unknown Structure 176XX. 1-Halogeno- and 1,4-Dihalogenophthalazines 1781. 1-Halogenophthalazines 1782. 1,4-Dihalogenophthalazines 179XXI. l-Aminophthalazines 183XXII. Reduced Phthalazines 1861. 3,4-Dihydrophthalazines  1862. 1,2,3,4-Tetrahydrophthalazines 189XXIII. Condensed Phthalazines and Azaphthalazines 1911. 1',2'-3,4-Benziminazolo-3,4-dihydrophthalazines 1912. Compounds Prepared from 1,4-Diketones 1923. Miscellaneous Compounds 1964. Azaphthalazines 198Part III. OuinoxalinesXXIV. Preparation of Ouinoxalines from Primary Aromatic o-Di-amines and 1,2-Dicarbonyl Compounds 203XXV. Ouinoxalines Unsubstituted in the Hetero Ring 228Quinoxaline 2286,6'-DiquinoxaIyl 229XXVI. Quinoxaline A’-Oxides 232A. Preparation 232B. Properties 232XXVII. 2-Hydroxy- and 2,3-Dihydroxyquinoxalines 2351. 2-Hydroxyquinoxalines 235A. Compounds Containing No Additional Substituent in the Hetero Ring 235B. Compounds Containing an Additional (C3) Substituent in the Hetero Ring 236Methylation of Hydroxyquinoxalines 2412. 2,3-Dihydroxyquinoxalines 242XXVIII. Quinoxaline-2-aldehydes 246A. Preparation 246B. Properties 246C. 3-Hydroxyquinoxaline-2-aldehyde 246XXIX. Quinoxaline-2-carboxyIic and-2,3-dicarboxylic Acids 2501. Quinoxaline-2-earboxylic Acids 2502. Quinoxaline-2,3-dicarboxyIic Acids 254XXX. 2-Chloro- and 2,3-Dichloroquinoxallnes 2581. 2-Chloroquinoxalines 2582. 2,3-Dihalogenoquinoxalines 260A. 2,3-DichIoroquinoxalines 260B. 2,3-Dibromoquinoxaline 261XXXI. 2-Amino- and 2,3-Diaminoquinoxatines  2631. 2-Aminoquinoxalines 263A. Primary Amino Compounds 263B. Secondary Amino Compounds 264C. 2-SulfonmidoquinoxaIines 265D. Tertiary Amino Compound 2652. Diaminoquinoxalines 265A. Diprimary Amino Compounds 2652.3- Diaminoquinoxaline 2652.3- Diaminoquinoxaline-6-arsonic Acid 267B. Primary-Secondary Amino Compounds 267C. Disecondary Amino Compounds 269XXXII. 2-Alkoxy-, 2,3-Dialkoxy-, and 2,3-Diaryloxyquinoxalines 2701. 2-AlkoxyquinoxaIines 2702. 2,3-Dialkoxy-and 2,3-Diaryloxyquinoxalines 271XXXIII. 2-Methyl- and 2,3-Dimethylquinoxalines 2731. 2-Methylquinoxalines 2732. 2,3-Dimethylquinoxalines 277XXXIV. Quinoxaline Quaternary Salts 286A. Preparation 286B. Properties 288C. Decomposition by Alkali 290D. Quinoxaline Cyanines 290XXXV. Formation of Quinoxalines from Compounds Containing a Furan Ring 2931. Conversion of 5-Hydroxy-2,5-diphenyl-4-keto-4,5-dihydrofurans and Related Compounds into Quinoxalines 2932. Conversion of Coumaran-3-ones into Quinoxalines 296A. 2-Hydroxy- and 2-Bromocoumaran-3-ones 296B. Coumaran-2,3-diones 298XXXVI. 2-Polyhydroxyalkylquinoxalines 3001. Synthesis 3002. Properties and Reactions 302A. General 302B. Decomposition by Alkali 304C. Reactions with Phenylhydrazine 306XXXVII. Reduced Quinoxalines 3101. 1,2-and 1,4-Dihydroquinoxalines 310A. Compounds Containing No Hydroxyl or Carbonyl Group in the Hetero Ring 310B. Compounds Containing a Hydroxyl or Carbonyl Group in the Hetero Ring 310(a) l-Substituted-2-keto-1,2-dihydroquinoxalines 310(b) 1,2- and 1,4-Dihydroqu inoxalines Having Hydroxyl Groups at C2 or C3 3182. 1,2,3,4-Tetrahydroquinoxalines 325A. 1,2,3,4-Tetrahydroquinoxalines Containing No Oxygen Atom Attached to the Hetero Ring 325Preparation 325Properties 326Stereoisomerism of 1,2,3,4-Tetrahydroquinoxalines 326I,4-EndoalkyIene-l,2,3,4-tetrahydroquinoxalines 326B. 1,2,3,4-Tetrahydroquinoxalines Containing an Oxygen Atom Attached to the Hetero Ring 329XXXVIII. Condensed Quinoxalines 3321. Quinoxalines Condensed with Carboeyclie Rings 332A. 5,6-Benzoquinoxalines 332B. 5,6,7,8-Dibenzoquinoxalines 338C. Glucazidone and Derivatives 338D. Other Condensed Quinoxalines 3412. Quinoxalines Condensed with Nitrogenous Heterocyclic Rings 346A. Pyrroloquinoxalines 346B. Pyridoquinoxalines 348C. Pyrazoloquinoxalines (Flavazoles) 348D. Glyoxalinoquinoxalines 353E. Triazoloquinoxalines 353F. Pyridazoquinoxalines 354XXXIX. Azaquinoxalines 356Appendix I. Ultraviolet Absorption Spectra of Cinnoiine and Quinoxaline Derivatives 358Appendix II. Basic Strengths of Cinnoiine, Phthalazine, and Quinoxaline Derivatives 363Appendix III. Antibacterial and Parasiticidal Activities of Cinnoiine and Quinoxaline Derivatives 364Index 367