The Chemistry of Heterocyclic Compounds

Sections

1. The Heterocyclic Derivatives of Phosphorus, Arsenic, Antimony, Bismuth, and Silicon 1950
2. Six-Membered Heterocyclic Nitrogen Compounds with Four Condensed Rings 1951
3. Thiophene and its Derivatives 1952
4. Five-Membered Heterocyclic Compounds with Nitrogen and Sulfur or Nitrogen, Sulfur, and Oxygen (Except Thiazole) 1952
5. Pyridazine and Pyrazine Rings: (Cinnolines, Phthalazines, and Quinoxalines) 1953
6. Imidazole and Its Derivatives, Part I, 1953
7. Compounds with Condensed Thiophene Rings, 1954
8. Heterocyclic Compounds with Indole and Carbazole Systems 1954
10. The 1,2,3- and 1,2,4-Triazines, Tetrazines & Pentazines, 1956
11. Phenazines, 1957
12. Six-Membered Heterocyclic Nitrogen Compounds with Three Condensed Rings 1958
13. s-Triazines and Derivatives, 1959
14. Pyridine and its Derivatives, Part One, 1960; Part Two, 1961; Part Three, 1962; Part Four, 1964; Part Five, 1985; Part 6: Pyridine Metal Complexes, 1985; Supplement Part One, 1974; Supplement Part Two, 1974; Supplement Part Three, 1974; Supplement Part Four, 1975
15. Heterocyclic Systems with Bridgehead Nitrogen Atoms, Part 2, 1961
16. The Pyrimidines, 1962; Supplement 1, 1970, Supplement II, 1985
17. Five- and Six-Membered Compounds with Nitrogen and Oxygen (Excluding Oxazoles), 1962
18. Chemistry of Heterocyclic Compounds: The Cyanine Dyes and Related Compounds, 1964
19. Heterocyclic Compounds with Three- and Four-Membered Rings Part 1 1964; Part 2 1964
20. Pyrazolones, Pyrazolidones, and Derivatives, 1964
21. Multi-Sulfur and Sulfur and Oxygen Five- and Six-Membered Heterocycles, Part 1, 1966; Part 2, 1966
22. Pyrazoles, Pyrazolines, Pyrazolidines, Indazoles and Condensed Rings, 1967
23. Furopyrans and Furopyrones, 1967
24. Fused Pyrimidines, Part I: Quinazolines, 1967; Part III: Pteridines, 1988; Part Four: Miscellaneous Fused Pyrimidines, 1992
25. Indoles, Part One, 1971; Part Two, 1971, Part Three, 1979; Part Four: The Monoterpenoid Indole Alkaloids, 1983
26. Seven-Membered Heterocyclic Compounds Containing Oxygen and Sulfur 1972
27. Condensed Pyridazines Including Cinnolines and Phthalazines, 1973
28. Pyridazines, 1973
29. Benzofurans, 1974
30. Special Topics in Heterocyclic Chemistry, 1977
31. Chromenes, Chromanones, and Chromones, 1977
32. Quinolines, Part I, 1977; Part II, 1982, Part III 1990
33. Chemistry of 1,2,3-Triazines and 1,2,4-Triazines, Tetrazines, and Pentazin, 1978
34. Thiazole and its Derivatives, Part One, 1979; Part Two, 1979; Part Three, 1979
35. Condensed Pyrazines, 1979
36. Chromans and Tocopherols, 1981
37. Triazoles 1,2,4, 1981
38. Isoquinolines, Part 1, 1981; Part 2, 1990
39. Triazoles 1,2,3, 1980
40. Benzimidazoles and Cogeneric Tricyclic Compounds, Part 1, 1981; Part 2, 1981
41. The Pyrazines, 1982
42. Small Ring heterocycles, Part 1: Aziridines, Azirines, Thiiranes, Thiirenes, 1983; Part 2: Azetidines, β-Lactams, Diazetidines, and Diaziridines, 1983; Part 3: Oxiranes, Arene Oxides, Oxaziridines, Dioxetanes, Thietanes, Thietes, Thiazetes, and Others 1985
43. Azepines, Part 1, 1984; Part 2, 1984
44. Thiophene and its Derivatives, Part One, 1985; Part Two, 1986; Part Three, 1986; Part Four, 1991 Part Five, 1992
45. Oxazoles, 1986
46. Condensed Imidazoles: 5-5 Ring Systems, 1986
47. Synthesis of Fused Heterocycles and Others 1987; Part 2, 1992
48. Pyrroles, Part One: The Synthesis and the Physical and Chemical Aspects of the Pyrrole Ring, 1990; Part 2: The Synthesis, Reactivity, and Physical Properties of Substituted Pyrroles, 1992
49. Isoxazoles Part One 1991; Part Two, 1999
50. Bicyclic Diazepines: Diazepines with an Additional Ring 1991
51. Aza-Crown Macrocycles 1993
52. The Pyrimidines, 1994
53. Tellurium-Containing Heterocycles 1994
54. The Purines, Supplement 1, 1996
55. Quinazolines, Supplement I, 1996
56. Monocyclic Azepines: The Syntheses and Chemical Properties of the Monocyclic Azepines 1996
57. The Pyridazines, Supplement 1, 2000
58. The Pyrazines: Supplement I, 2002
59. Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, 2002
60. Oxazoles: Synthesis, Reactions, and Spectroscopy, 2003
61. Quinoxalines: Supplement II, 2004
62. The Chemistry of 1,2,3-Thiadiazoles, 2004
63. The Naphthyridines, 2007
64. Cinnolines and Phthalazines: Supplement II, 2005

Index

1. The Heterocyclic Derivatives of Phosphorus, Arsenic, Antimony, Bismuth, and Silicon🌐 Mann FG
   1. Heterocyclic Derivatives of Phosphorus 9
   2. Heterocyclic Derivatives of Arsenic 25
   3. Heterocyclic Derivatives of Antimony 129
   4. Heterocyclic Derivatives of Bismuth 157
   5. Heterocyclic Derivatives of Silicon 161
2. Six-Membered Heterocyclic Nitrogen Compounds with Four Condensed Rings🌐 Allen CFH
   1. Azanaphthacenes Webster ER 3
   2. Azabenz[a]anthracenes Crawford JV, Webster ER 57
   3. Azabenzo[c]phenanthrenes Webster ER 133
   4. Azachrysenes Crawford JV 151
   5. Azatriphenylenes Crawford JV 185
   6. Azabenzanthrenes Allen CFH, Burness DM, Spangler FW 201
   7. Azapyrenes Webster ER 295
   8. Azabenzanthrenes: Addendum Wilson CV 311
3. Thiophene and its Derivatives🌐 Hartough HD
   1. General Discussion 3
   2. Biological and Pharmacological Activity of Thiophene and Its Derivatives 29
   3. Synthesis and Physical Propperties of Thiophene and Its Homologs 47
   4. Molecular Structure and Spectroscopy of Thiophene and Its Derivatives Hochgesang FP 81
   5. Factors Affecting Substitution Reactions in the Thiophene Nucleus 143
   6. Alkylation, Polymerization, Hydrogenation and Miscellaneous Reactions of Thiophene 159
   7. Halothiophenes and Haloalkylthiophenes 173
   8. The Nitro- and Aminothiophenes 219
   9. Thiophene Compounds Containing Nitrogen in the Side Chain 241
   10. Hydroxythiophenes, Thienylalkanols, Alkoxythiophenes, and Thienyl-alkyl Ethers 287
   11. Aldo and Keto Derivatives of Thiophene 307
   12. Carboxy Derivatives of Thiophene 363
   13. Sulfur Derivatives of Thiophene 417
   14. Metal and Miscellaneous Metalloid Derivatives of Thiophene 439
   15. Synthesis and Properties of Di- and Polythienyls and Arylthiophene 459
   16. Selenophene, Tetrahydroselenophene, Telllurophene, and Tetrahydrotellurophene 479
   17. Appendix. Laboratory Preparations of Thiophene Compounds 495
4. Five-Membered Heterocyclic Compounds with Nitrogen and Sulfur or Nitrogen, Sulfur, and Oxygen (Except Thiazole)🌐 Bambas LL
   • Part I - Thiadiazoles, Their Derivatives and Selenium Analogs
   • Derivatives of the 1,2,3-Thiadiazoles and Their Selenium Analogs 3
   • Derivatives of the 1,2,4-Thiadiazoles and Their Selenium Analogs 35
   • Derivatives of the 1,3,4-Thiadiazoles and Their Selenium Analogs 81
   • Derivatives of the 2,1,3-Thiadiazoles and Their Selenium Analogs 205
   • Part II - Five-Membered Rings Containing Nitrogen, SUlfur, Selenium, or Oxygen Atoms in Addition to One Sulfur and One Nitrogen 215
   • Part III - Isothiazoles, Their Derivatives and Selenium Analogs
   • 2,1-Benzoisothiazoles 225
   • 1,2-Benzoisothiazoles, Their Homologs and Selenium Analogs 227
   • 1,2-Benzoisosulfonazoles, Their Homologs and Derivatives ?
5. Pyridazine and Pyrazine Rings: (Cinnolines, Phthalazines, and Quinoxalines)🌐 Simpson JCE
   • Part I. Cinnolines
     1. General Introduction to Cinnoline Derivatives. Preparation and Properties of Cinnoline 3
     2. 4-Aryl-, 4-Acyl, and 4-Carboxycinnolines 6
     3. 4-Methylcinnolines 13
     4. 4-Hydroxycinnolines 16
     5. 4-Chloro, 4-Alkoxy, and 4-Phenoxycinnolines 29
     6. 4-Aminocinnolines 35
     7. Cinnoline Quaternary Salts 39
     8. Reduced Cinnolines 46
     9. Cinnolines Containing Additional Fused Rings 52
   • Part II. Phthalazines
     10. Phthalazines Unsubstituted in the Hetero Ring 69
     11. 1-Alkyl-, 1-Aryl-, and 1,4-Diarylphthalazines 72
     12. 1-Hydroxyphthalazines 78
     13. Alkyl, Aryl, and Acyl Derivatives of 4-(1-)Hydroxyphthalazines 84
     14. 1-Hydroxy-3-aryl-3,4-dihydrophthalazine-4-acetic Acids 106
     15. 3-Aryl-1-ketophthalazines 119
     16. Methylated Derivatives of 3-Aryl-1-ketophthalazines 130
     17. 1,4-Dihydroxyphthalazines 140
     18. Monoalkyl and Monoacyl Derivatives of 1,4-Dihydroxyphthalazines 157
     19. Dialkyl and Diacyl Derivatives of 1,4-Dihydroxyphthalazines 168
     20. 1-Halogeno- and 1,4-Dihalogenophthalazines 178
     21. 1-Aminophthalazines 183
     22. Reduced Phthalazines 186
     23. Condensed Phthalazines and Azaphthalazines 191
   • Part III. Quinoxalines
     24. Preparation of Quinoxalines from Primary Aromatic o-Diamines and 1,2-Dicarbonyl Compounds 203
     25. Quinoxalines Unsubstituted in the Hetero Ring 228
     26. Quinoxaline N-Oxides 232
     27. 2-Hydroxy- and 2,3-Dihydroxyquinoxalines 235
     28. Quinoxaline-2-aldehydes 246
     29. Quinoxaline-2-carboxylic and -2,3-dicarboxylic Acids 250
     30. 2-Chloro- and 2,3-Dichloroquinoxalines 258
     31. 2-Amino- and 2,3-Diaminoquinoxalines 263
     32. 2-Alkoxy-, 2,3-Dialkoxy-, and 2,3-Diaryloxyquinoxalines 270
     33. 2-Methyl- and 2,3-Dimethylquinoxalines 273
     34. Quinoxaline Quaternary Salts 286
     35. Formation of Quinoxalines from Compounds Containing a Furan Ring 293
     36. 2-Polyhydroxyalkylquinoxalines 300
     37. Reduced Quinoxalines 310
     38. Condensed Quinoxalines 332
     39. Azaquinoxalines 356
   • Appendix I Ultraviolet Absorption Spectra of Cinnoline and Quinoxaline Derivatives358
   • Appendix II Basic Strenghts of Cinnoline, Phthalazine, and Quinoxaline Derivatives363
   • Appendix III Antibacterial and Parasiticidal Acitivities of Cinnoline and Quinoxaline Derivatives364
8. Heterocyclic Compounds with Indole and Carbazole Systems🌐 Sumpter WC, Miller FM
   1. Indole 1
   2. Carbazole 70
   3. Isatin 110
   4. Oxindole 134
   5. Isatogens 154
   6. Indoxyl 163
   7. Indigo 171
   8. Natural Products Containing the Indole Nucleus 196
12. Six-Membered Heterocyclic Nitrogen Compounds with Three Condensed Rings🌐 Allen CFH
    1. Azaanthracenes Wilson CV 14
    2. Azaphenanthrenes Thirtle JR 165
    3. 4-Azaphenanthrenes Van Allan JA 216
    4. 5-Azaphenanthrenes Van Allan JA 271
    5. Diazaphenanthrenes (except Phenanthrolines) Thirtle JR 320
    6. 1,10-, 1,7- and 4,7-Diazaphenanthrenes Graham B 386
    7. Other Polyazaphenanthrenes Thirtle JR 457
    8. Azabenzonaphthenes Richmond JH 484
    9. The Ultraviolet Absorption Spectra of Polycyclic Heterocyclic Aromatic Compounds Badger GM 551
    10. Naphthalimides: Addendum Alllen CFH 567
19. Heterocyclic Compounds with Three- and Four-Membered Rings, Part 1🌐 Weissberger A
    1. Ethylene Oxides Rosowsky A 1
    2. Aziridines Fanta PE 524
    3. Ethylene Sulfides Reynolds DD, Fields DL 576
    4. Oxaziranes Emmons WD 624
19. Heterocyclic Compounds with Three- and Four-Membered Rings, Part 2🌐 Weissberger A
    5. Thietane and Its Derivatives Etienne Y, Soulas R, Lumbroso H 647
    6. β-Lactones Etienne Y, Fischer N 729
    7. Trimethyleneimines Moore JA 885
    8. Four-Membered Rings Containing Two Heteroatoms Emmons WD 978
    9. Oxetanes Searles Jr S 983
20. Seven-Membered Heterocyclic Compounds Containing Oxygen and Sulfur🌐 Rosowsky A
    1. Oxepins and Related Oxepins 1
    2. Oxepine Ring Systems Contining Two Rings 51
    3. Oxepin Ring Systems Contining Three Rings 136
    4. Oxepin Ring Systems Contining More Than Three Rings 259
    5. Dioxepins and Trioxepins 319
    6. Terpene Oxepins 412
    7. Steroidal Oxepins 467
    8. Oxepins Derived from Sugars 521
    9. Alkaloids Containing a Seven-Membered Oxygen Ring 560
    10. Monocyclic Seven-Membered Rings Containing Sulfur 573
    11. Condensed Thiepins 667
42. Small Ring Heterocycles Part 3
    Oxiranes, Arene Oxides, Oxaziridines, Dioxetanes, Thietanes, Thietes, Thiazetes, and Others🌐 Hassner A
    1. Oxiranes Bartok M, Lang KL 1
    2. Arene Oxides-Oxepins Boyd DR, Jerina DM 197
    3. Oxaziridines Haddadin MJ, Freeman JP 283
    4. 1,2-Dioxetanes and α-Peroxylactones Adam W, Yany F 351
    5. Four-Membered Sulfur Heterocycles Dittmer DC, Sedergran TC 431
47. Synthesis of Fused Heterocycles and Others🌐 Ellis GP
49. Isoxazoles Part One🌐 Grünanger P, Vita-Finzi P
    1. Isoxazoles 1
    2. Isoxazolines (Dihydroisoxazoles) 417
    3. Isoxazolidines (Tetrahydroisoxazoles) 649
50. Bicyclic Diazepines: Diazepines with an Additional Ring🌐 Fryer RI
    1. Bicyclic-1,2-Diazepines Fryer RI, Walser A 1
    2. Bicyclic-1,3-Diazepines Fryer RI, Walser A 89
    3. 1,4-Diazepines with [a]- or [d]-Fused Rings Fryer RI, Walser A 183
    4. [1,4]Diazepines with [b]-Fused Rings Fryer RI, Walser A 209
    5. 1,4-Benzodiazepines Walser A, Fryer RI 431
    6. Dihydro-1,4-Benzodiazepines Walser A, Fryer RI 545
    7. Dihydro-1,4-Benzodiazepinones and Thiones Walser A, Fryer RI 631
    8. Tetrahydro- and Polyhydro-1,4-Benzodiazepines Walser A, Fryer RI 849
    9. Hetero Ring[e][1,4]Diazepines Walser A, Fryer RI 947
51. Aza-Crown Macrocycles🌐 Bradshaw JS, Krakowiak KE, Izatt RM
    1. Aza-Crown Macrocycles: An Overview 1
    2. Preparation of Starting Materials 31
    3. General Synthetic Methos for the Polyaza-Crown Macrocycles 73
    4. Common Methods for the Formation of Polyaza Macrocyclic Rings 123
    5. Monoaza-Crown Macrocycles 173
    6. Diaza-Crown Macrocycles 245
    7. Polyaza-Crown Macrocycles 349
    8. Benzoaza-Crown Macrocycles 401
    9. Aza-Crown Macrocycles Containing Other Heteratoms in the Macroring 471
    10. Aliphatic Peraza-Crown Macrocycles (Cyclams) 539
    11. Peraza-Cyclophanes 693
    12. Aza- and Peraza-Crown Macrocycles as Part of Macromolecular Compounds 693
    13. Some Practical Approaches to the Aza-Crown Macrocycles 795
53. Tellurium-Containing Heterocycles🌐 Detty MR, O'Regan MB
    1. Tellurium-Containing Heterocycles: Reviews, Distinguishing Features, and Utility 1
    2. Tellurophenes, Dihydrotellurophenes, and Tetrahydrotellurophenes and Their Benzo and Dibenzo Analogs 31
    3. Telluranes, Tellurins, and Other Six-Membered Rings Containing One Tellurium Atom 147
    4. Telluropyrylium Compounds 219
    5. Tellurium-Containing Heterocycles with at Least One Group Va Element (Nitrogen, Phosphorus, or Arsenic) 293
    6. Tellurium-Containing Heterocycles Composed of Group IVa (Carbon, Silicon, Germanium, and Tin) and Group VIa Elements (Tellurium, Selenium, Sulfur, and Oxygen) 325
    7. Tellurium-Containing Heterocycles as Donor Molecules 363
    8. Tellurium-Containing Heterocycles with Hypervalent or Coordination Bonds to Tellium 425
56. Monocyclic Azepines: The Syntheses and Chemical Properties of the Monocyclic Azepines🌐 Proctor GR, Redpath J
    2. Azepanes (Hexahydroazepines) 9
    3. Azepanones 117
    4. Azepanediones 251
    5. Tetrahydroazepines 288
    6. Tetrahydroazepinones 288
    7. Tetrahydroazepinediones 403
    8. Dihydroazepines 412
    9. Dihydroazepinones 449
    10. Dihydroazepinediones 481
    11. Azepines 487
    12. Azepinones 592