Detailed table of contents (pdf)
Detailed table of contents (pdf) Detailed table of contents (pdf)
XLVI Table of Contents 17.4.5.2.1.5 Of Six-Membered Arenes .................................................. 776 17.4.5.2.1.5.1 Method 1: Intramolecular Insertion of Arylnitrenes .................... 776 17.4.5.2.1.5.1.1 Variation 1: Thermal Decomposition of Aryl Azides ..................... 776 17.4.5.2.1.5.1.2 Variation 2: Photolytic Decomposition of Aryl Azides ................... 778 17.4.5.2.1.5.1.3 Variation 3: Deoxygenation of Nitrosoarenes ........................... 783 17.4.5.2.1.5.1.4 Variation 4: Deoxygenation of Nitroarenes ............................. 784 17.4.5.2.1.5.1.5 Variation 5: Thermal Decomposition of N-Phenyl-N,O-bis(trimethylsilyl)hydroxylamine ........................................ 787 17.4.5.2.1.5.2 Method 2: From the Insertion of Nitrenes into Arenes ................. 787 17.4.5.2.1.5.2.1 Variation 1: Thermolysis of Azidoformates ............................. 788 17.4.5.2.1.5.2.2 Variation 2: Pyrolysis of 2-Haloindan-1-yl Azidoformates ................ 790 17.4.5.2.1.5.2.3 Variation 3: Photolysis of Azidoformates ............................... 791 17.4.5.2.1.5.2.4 Variation 4: Decomposition of N-[(4-Nitrophenyl)sulfonyloxy]carbamates 792 17.4.5.2.1.5.2.5 Variation 5: Thermolysis of Arenesulfonyl Azides ........................ 792 17.4.5.2.1.5.2.6 Variation 6: Reaction of Phthalimidonitrene with Activated Benzenes .... 796 17.4.5.2.1.5.2.7 Variation 7: Thermolysis of Cyanogen Azide ............................ 796 17.4.5.2.1.5.2.8 Variation 8: Deoxygenation of Nitrosobenzenes and Nitrosoformates .... 797 17.4.5.2.1.5.2.9 Variation 9: Photolysis of 2-Azido-1,3,5-triazines ....................... 798 17.4.5.2.1.5.3 Method 3: From Anilides ............................................. 798 17.4.5.3 Aromatization ............................................................ 800 17.4.5.3.1 Method 1: Isomerization with Meerwein s Reagent .................... 800 17.4.5.3.1.1 Variation 1: Of 1,5-Dihydro-2H-azepin-2-ones .......................... 800 17.4.5.3.1.2 Variation 2: Of 1,2-Dihydro-3H-azepin-3-ones .......................... 801 17.4.5.3.2 Method 2: Bromination–Dehydrobromination of 4-Ethoxy-1,2,6,7-tetrahydrocyclopent[d]azepine ............ 801 17.4.5.3.3 Method 3: Dehydrobromination of 3,6-Dibromo-1-phenyl-2,3,6,7tetrahydro-1H-phosphepin 1-Oxide ........................ 802 17.4.5.4 Synthesis by Substituent Modification ..................................... 803 17.4.5.4.1 Substitution of Existing Substituents ....................................... 803 17.4.5.4.1.1 Of Hydrogen .............................................................. 803 17.4.5.4.1.1.1 Method 1: Tautomerization .......................................... 803 17.4.5.4.1.1.1.1 Variation 1: Rearrangement of 1H- to3H-Azepines ..................... 803 17.4.5.4.1.1.1.2 Variation 2: Rearrangement of 2H- to3H-Azepines ..................... 804 17.4.5.4.1.1.1.3 Variation 3: Rearrangement of 4H- to3H-Azepines ..................... 805 17.4.5.4.1.1.1.4 Variation 4: Rearrangement of 3H- to3H-Azepines ..................... 805 17.4.5.4.1.1.2 Method 2: Metalation ................................................ 807 17.4.5.4.1.1.3 Method 3: C-Acylation ............................................... 807 17.4.5.4.1.1.4 Method 4: C-Alkylation .............................................. 808 17.4.5.4.1.1.5 Method 5: C-Halogenation ........................................... 810 17.4.5.4.1.1.6 Method 6: C-Thiolation .............................................. 811 17.4.5.4.1.1.7 Method 7: C-Amination .............................................. 811 17.4.5.4.1.1.8 Method 8: N-Substitution ............................................ 812 17.4.5.4.1.2 Of Carbon Functionalities ................................................. 812 17.4.5.4.1.2.1 Method 1: N-Decarboxylation ........................................ 812 17.4.5.4.1.3 Of Heteroatoms .......................................................... 813
Table of Contents XLVII 17.4.5.4.1.3.1 Method 1: Of Alkoxy Groups ......................................... 813 17.4.5.4.1.3.2 Method 2: Of Sulfur or Silyl on the Ring Nitrogen ...................... 814 17.4.5.4.1.3.3 Method 3: Of Amino Groups ......................................... 814 17.4.5.4.2 Addition Reactions ....................................................... 815 17.4.5.4.2.1 Method 1: Preparation of Azepine–Metal Complexes .................. 815 17.4.5.4.2.2 Method 2: N-Oxidation .............................................. 816 17.4.5.4.3 Modification of Substituents .............................................. 816 17.4.5.4.3.1 Method 1: Condensation Reactions ................................... 816 17.4.5.4.3.2 Method 2: Hydrolysis of Esters and Nitriles ............................ 817 17.4.5.4.3.3 Method 3: Oxidations ................................................ 818 17.4.5.4.3.4 Method 4: Reductions ............................................... 818 17.4.6 Product Subclass 6: Benzazepines and Their Group 15 Analogues J.-P. K. Meigh 17.4.6 Product Subclass 6: Benzazepines and Their Group 15 Analogues ........ 825 17.4.6.1 1H-1-Benzazepines ....................................................... 831 17.4.6.1.1 Synthesis by Ring-Closure Reactions ....................................... 831 17.4.6.1.1.1 By Formation of One N—C and One C—C Bond ............................. 831 17.4.6.1.1.1.1 Method 1: From N-Methylaniline and Levulinic Acid .................... 831 17.4.6.1.1.1.2 Method 2: Lewis Acid Catalyzed Dimerization of Pentafluoroaniline .... 831 17.4.6.1.1.2 By Formation of Two C—C Bonds .......................................... 832 17.4.6.1.1.2.1 Method 1: By Thermal Cycloaddition of Dimethyl Acetylenedicarboxylate with 1-Methylindole ....................................... 832 17.4.6.1.1.2.1.1 Variation 1: By Thermal Cycloaddition of Acetylene Esters with 1-Acetyl-3-piperidin-1-yl-1H-indole ........................ 834 17.4.6.1.1.2.1.2 Variation 2: By Photocycloaddition of Dimethyl Acetylenedicarboxylate with 1-Methylindole ....................................... 835 17.4.6.1.1.2.2 Method 2: From the Reaction of 2-Substituted Quinoline Oxides with Dimethyl Acetylenedicarboxylate .......................... 836 17.4.6.1.1.3 By Formation of One C—C Bond ........................................... 837 17.4.6.1.1.3.1 Method 1: By Intramolecular Aldol Condensation ...................... 837 17.4.6.1.2 Synthesis by Ring Transformation .......................................... 838 17.4.6.1.2.1 By Ring Enlargement ..................................................... 838 17.4.6.1.2.1.1 Method 1: Thermolysis of 2a,7b-Dihydro-3H-cyclobut[b]indoles ........ 838 17.4.6.1.2.1.1.1 Variation 1: By Thermal Valence Isomerization of 2a,7b-Dihydro-3Hcyclobut[b]indoles ........................................ 839 17.4.6.1.3 Aromatization ............................................................ 840 17.4.6.1.3.1 Method 1: By Electrochemical Oxidation of 2,5-Dihydro-1H-1-benzazepines .................................................. 840 17.4.6.1.3.2 Method 2: By Chemical Oxidation of 5a,9a-Dihydro-1H-1-benzazepines 840
- Page 1 and 2: Table of Contents IX Volume 17: Six
- Page 3 and 4: Table of Contents XI Table of Conte
- Page 5 and 6: Table of Contents XIII 17.1.1.2.4.1
- Page 7 and 8: Table of Contents XV 17.1.2.3.1.3 B
- Page 9 and 10: Table of Contents XVII 17.1.3.2 1,4
- Page 11 and 12: Table of Contents XIX 17.1.3.3.1.1.
- Page 13 and 14: Table of Contents XXI 17.2 Product
- Page 15 and 16: Table of Contents XXIII 17.2.1.2.1.
- Page 17 and 18: Table of Contents XXV 17.2.1.3.1.1
- Page 19 and 20: Table of Contents XXVII 17.2.2 Prod
- Page 21 and 22: Table of Contents XXIX 17.2.2.1.3.3
- Page 23 and 24: Table of Contents XXXI 17.2.2.2.1.4
- Page 25 and 26: Table of Contents XXXIII 17.2.3.1.1
- Page 27 and 28: Table of Contents XXXV 17.2.3.1.2.2
- Page 29 and 30: Table of Contents XXXVII 17.2.3.1.4
- Page 31 and 32: Table of Contents XXXIX 17.3.3.2 Sy
- Page 33 and 34: Table of Contents XLI 17.4.2.2.2.2
- Page 35 and 36: Table of Contents XLIII 17.4.4.1.2.
- Page 37: Table of Contents XLV 17.4.5.1.2.3
- Page 41 and 42: Table of Contents XLIX 17.4.6.2.4.2
- Page 43 and 44: Table of Contents LI 17.4.6.5.4.2 A
- Page 45 and 46: Table of Contents LIII 17.4.6.7.4.4
- Page 47 and 48: Table of Contents LV 17.5.2.2.1 Met
- Page 49 and 50: Table of Contents LVII 17.6.2.1.1.4
- Page 51 and 52: Table of Contents LIX 17.6.5.2.2.1.
- Page 53 and 54: Table of Contents LXI 17.7.3.2 [2.3
- Page 55 and 56: Table of Contents LXIII 17.7.5.1.2.
- Page 57 and 58: Table of Contents LXV 17.8.3.2 Cont
- Page 59 and 60: Table of Contents LXVII 17.9.8.3 Me
- Page 61: Table of Contents LXIX 17.9.22.3 Me
Table <strong>of</strong> Contents XLVII<br />
17.4.5.4.1.3.1 Method 1: Of Alkoxy Groups ......................................... 813<br />
17.4.5.4.1.3.2 Method 2: Of Sulfur or Silyl on the Ring Nitrogen ...................... 814<br />
17.4.5.4.1.3.3 Method 3: Of Amino Groups ......................................... 814<br />
17.4.5.4.2 Addition Reactions ....................................................... 815<br />
17.4.5.4.2.1 Method 1: Preparation <strong>of</strong> Azepine–Metal Complexes .................. 815<br />
17.4.5.4.2.2 Method 2: N-Oxidation .............................................. 816<br />
17.4.5.4.3 Modification <strong>of</strong> Substituents .............................................. 816<br />
17.4.5.4.3.1 Method 1: Condensation Reactions ................................... 816<br />
17.4.5.4.3.2 Method 2: Hydrolysis <strong>of</strong> Esters and Nitriles ............................ 817<br />
17.4.5.4.3.3 Method 3: Oxidations ................................................ 818<br />
17.4.5.4.3.4 Method 4: Reductions ............................................... 818<br />
17.4.6 Product Subclass 6: Benzazepines and Their Group 15 Analogues<br />
J.-P. K. Meigh<br />
17.4.6 Product Subclass 6: Benzazepines and Their Group 15 Analogues ........ 825<br />
17.4.6.1 1H-1-Benzazepines ....................................................... 831<br />
17.4.6.1.1 Synthesis by Ring-Closure Reactions ....................................... 831<br />
17.4.6.1.1.1 By Formation <strong>of</strong> One N—C and One C—C Bond ............................. 831<br />
17.4.6.1.1.1.1 Method 1: From N-Methylaniline and Levulinic Acid .................... 831<br />
17.4.6.1.1.1.2 Method 2: Lewis Acid Catalyzed Dimerization <strong>of</strong> Pentafluoroaniline .... 831<br />
17.4.6.1.1.2 By Formation <strong>of</strong> Two C—C Bonds .......................................... 832<br />
17.4.6.1.1.2.1 Method 1: By Thermal Cycloaddition <strong>of</strong> Dimethyl Acetylenedicarboxylate<br />
with 1-Methylindole ....................................... 832<br />
17.4.6.1.1.2.1.1 Variation 1: By Thermal Cycloaddition <strong>of</strong> Acetylene Esters with<br />
1-Acetyl-3-piperidin-1-yl-1H-indole ........................ 834<br />
17.4.6.1.1.2.1.2 Variation 2: By Photocycloaddition <strong>of</strong> Dimethyl Acetylenedicarboxylate<br />
with 1-Methylindole ....................................... 835<br />
17.4.6.1.1.2.2 Method 2: From the Reaction <strong>of</strong> 2-Substituted Quinoline Oxides with<br />
Dimethyl Acetylenedicarboxylate .......................... 836<br />
17.4.6.1.1.3 By Formation <strong>of</strong> One C—C Bond ........................................... 837<br />
17.4.6.1.1.3.1 Method 1: By Intramolecular Aldol Condensation ...................... 837<br />
17.4.6.1.2 Synthesis by Ring Transformation .......................................... 838<br />
17.4.6.1.2.1 By Ring Enlargement ..................................................... 838<br />
17.4.6.1.2.1.1 Method 1: Thermolysis <strong>of</strong> 2a,7b-Dihydro-3H-cyclobut[b]indoles ........ 838<br />
17.4.6.1.2.1.1.1 Variation 1: By Thermal Valence Isomerization <strong>of</strong> 2a,7b-Dihydro-3Hcyclobut[b]indoles<br />
........................................ 839<br />
17.4.6.1.3 Aromatization ............................................................ 840<br />
17.4.6.1.3.1 Method 1: By Electrochemical Oxidation <strong>of</strong> 2,5-Dihydro-1H-1-benzazepines<br />
.................................................. 840<br />
17.4.6.1.3.2 Method 2: By Chemical Oxidation <strong>of</strong> 5a,9a-Dihydro-1H-1-benzazepines 840
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