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XLVIII Table <strong>of</strong> Contents<br />

17.4.6.1.3.3 Method 3: By Chlorination–Dehydrochlorination <strong>of</strong> Phenyl-2,3,4,5tetrahydro-1H-benzazepin-2-ones<br />

......................... 841<br />

17.4.6.1.4 Synthesis by Substituent Modification ..................................... 843<br />

17.4.6.1.4.1 Substitution <strong>of</strong> Existing Substituents ....................................... 843<br />

17.4.6.1.4.1.1 Method 1: Bromination <strong>of</strong> 1H-1-Benzazepines ......................... 843<br />

17.4.6.1.4.1.2 Method 2: Acetylation <strong>of</strong> 1H-1-Benzazepine ........................... 843<br />

17.4.6.2 2-Benzazepines .......................................................... 844<br />

17.4.6.2.1 Synthesis by Ring-Closure Reactions ....................................... 844<br />

17.4.6.2.1.1 By Formation <strong>of</strong> One N—C and One C—C Bond ............................. 844<br />

17.4.6.2.1.1.1 Method 1: From (Z)-3-(Tributylstannyl)allylamine and Aryl Bromides ... 844<br />

17.4.6.2.1.1.2 Method 2: From 1,3-Monoazabisylides and Phthalaldehyde ............ 844<br />

17.4.6.2.1.1.3 Method 3: From Cycloaddition <strong>of</strong> Inden-2-one and 2H-Azirines ......... 845<br />

17.4.6.2.1.2 By Formation <strong>of</strong> One N—C Bond ........................................... 846<br />

17.4.6.2.1.2.1 Method 1: By Partial Reduction <strong>of</strong> Acetylenic Benzophenones .......... 846<br />

17.4.6.2.1.3 By Formation <strong>of</strong> One C—C Bond ........................................... 847<br />

17.4.6.2.1.3.1 Method 1: By Photoisomerization <strong>of</strong> 3-Phenyl-2-[(Z)-2-phenylvinyl]-2Hazirene<br />

................................................... 847<br />

17.4.6.2.1.3.2 Method 2: By 1,7-Electrocyclization <strong>of</strong> Diene-Conjugated Nitrile Ylides . 847<br />

17.4.6.2.2 Synthesis by Ring Transformation .......................................... 848<br />

17.4.6.2.2.1 By Ring Enlargement ..................................................... 848<br />

17.4.6.2.2.1.1 Method 1: Base-Mediated Ring Expansion <strong>of</strong> 1,4-Dihydro-4-(hydroxymethyl)[c]isoquinolines<br />

................................... 848<br />

17.4.6.2.2.1.2 Method 2: By Thermolysis <strong>of</strong> Dihydrocyclopropa[c]isoquinolines ....... 849<br />

17.4.6.2.2.1.2.1 Variation 1: From 1,4-Dihydro-4-(hydroxymethyl)[c]isoquinolines and<br />

Silver(I) Trifluoroacetate ................................... 850<br />

17.4.6.2.2.1.3 Method 3: Deoxygenation <strong>of</strong> Nitroarenes ............................. 850<br />

17.4.6.2.2.1.4 Method 4: Photolysis <strong>of</strong> Aryl Azides ................................... 851<br />

17.4.6.2.3 Aromatization ............................................................ 852<br />

17.4.6.2.3.1 Method 1: By syn-Dehydrobromination ............................... 852<br />

17.4.6.2.4 Synthesis by Substituent Modification ..................................... 853<br />

17.4.6.2.4.1 Substitution <strong>of</strong> Existing Substituents ....................................... 853<br />

17.4.6.2.4.1.1 Of Hydrogen ............................................................. 853<br />

17.4.6.2.4.1.1.1 Method 1: By an Oxygen Functionality ................................ 853<br />

17.4.6.2.4.1.1.2 Method 2: By Tautomerism .......................................... 853<br />

17.4.6.2.4.1.2 Of Heteroatoms .......................................................... 853<br />

17.4.6.2.4.1.2.1 Method 1: Palladium(0)-Catalyzed Carboalkoxylation <strong>of</strong> 5-Bromo-<br />

5H-2-benzazepines ........................................ 853<br />

17.4.6.2.4.2 Addition Reactions ....................................................... 854<br />

17.4.6.2.4.2.1 Of Hydrogen .......................................................... 854<br />

17.4.6.2.4.2.2 Of Organic Groups ........................................................ 854

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