Detailed table of contents (pdf)
Detailed table of contents (pdf)
Detailed table of contents (pdf)
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LII Table <strong>of</strong> Contents<br />
17.4.6.7.1.1 By Formation <strong>of</strong> Two C—C Bonds .......................................... 888<br />
17.4.6.7.1.1.1 Method 1: From 2,2¢-Bis(bromomethyl)diphenylamine ................ 888<br />
17.4.6.7.1.1.1.1 Variation 1: From Bis(2¢-formylphenyl)amine ........................... 888<br />
17.4.6.7.2 Synthesis by Ring Transformation .......................................... 888<br />
17.4.6.7.2.1 By Ring Enlargement ..................................................... 888<br />
17.4.6.7.2.1.1 Method 1: From 1-Arylindoles ........................................ 888<br />
17.4.6.7.2.1.2 Method 2: From 9,10-Dihydroacridin-9-ylmethanol .................... 890<br />
17.4.6.7.2.1.2.1 Variation 1: From 9-(Hydroxymethyl)-9,10-dihydroacridine and Sulfuric<br />
Acid ...................................................... 891<br />
17.4.6.7.2.1.2.2 Variation 2: Base-Promoted Ring Expansion <strong>of</strong> Acridine Methanesulfonates<br />
................................................ 892<br />
17.4.6.7.3 Aromatization ............................................................ 893<br />
17.4.6.7.3.1 Method 1: Bromination–Dehydrobromination ......................... 893<br />
17.4.6.7.3.2 Method 2: Catalytic Dehydrogenation ................................ 893<br />
17.4.6.7.4 Synthesis by Substituent Modification ..................................... 894<br />
17.4.6.7.4.1 Substitution <strong>of</strong> Existing Substituents ....................................... 894<br />
17.4.6.7.4.1.1 Of Hydrogen .............................................................. 894<br />
17.4.6.7.4.1.1.1 Method 1: Nitration <strong>of</strong> 5H-Dibenz[b,f]azepines ........................ 894<br />
17.4.6.7.4.1.1.2 Method 2: Friedel–Crafts Acylation <strong>of</strong> 5-Acyl-5H-dibenz[b,f]azepines ... 895<br />
17.4.6.7.4.1.1.3 Method 3: N-Alkylation <strong>of</strong> 5H-Dibenz[b,f]azepines ..................... 895<br />
17.4.6.7.4.1.1.3.1 Variation 1: By Phase-Transfer Catalysis ................................ 896<br />
17.4.6.7.4.1.1.3.2 Variation 2: By Reductive Amination ................................... 896<br />
17.4.6.7.4.1.1.4 Method 4: N-Acylation <strong>of</strong> 5H-Dibenz[b,f]azepines ..................... 897<br />
17.4.6.7.4.1.1.5 Method 5: Chlorocarbonylation <strong>of</strong> 5H-Dibenz[b,f]azepines with<br />
Phosgene Equivalents ..................................... 897<br />
17.4.6.7.4.1.1.5.1 Variation 1: Reaction with Cyanogen Bromide .......................... 898<br />
17.4.6.7.4.2 Of Metals ................................................................ 898<br />
17.4.6.7.4.2.1 Method 1: Directed ortho-Metalation ................................. 898<br />
17.4.6.7.4.3 Of Heteroatoms .......................................................... 899<br />
17.4.6.7.4.3.1 Method 1: By Halogen–Lithium Exchange ............................. 899<br />
17.4.6.7.4.3.2 Method 2: Nucleophilic Displacement <strong>of</strong> Bromide ..................... 900<br />
17.4.6.7.4.3.2.1 Variation 1: Nucleophilic Displacement <strong>of</strong> Bromide by Nitrogen<br />
Nucleophiles (Aminodebromination) ....................... 900<br />
17.4.6.7.4.4 Addition Reactions ....................................................... 901<br />
17.4.6.7.4.4.1 Reduction Reactions ...................................................... 901<br />
17.4.6.7.4.4.1.1 Method 1: Reduction at the C10—C11 Double Bond ................... 901<br />
17.4.6.7.4.4.2 Of Heteroatoms .......................................................... 901<br />
17.4.6.7.4.4.2.1 Method 1: Halogenation ............................................. 901<br />
17.4.6.7.4.4.3 Oxidation Reactions ...................................................... 902<br />
17.4.6.7.4.4.3.1 Method 1: Formation <strong>of</strong> N-Oxides .................................... 902<br />
17.4.6.7.4.4.3.2 Method 2: Formation <strong>of</strong> Epoxides .................................... 902
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