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XLVIII Table of Contents 17.4.6.1.3.3 Method 3: By Chlorination–Dehydrochlorination of Phenyl-2,3,4,5tetrahydro-1H-benzazepin-2-ones ......................... 841 17.4.6.1.4 Synthesis by Substituent Modification ..................................... 843 17.4.6.1.4.1 Substitution of Existing Substituents ....................................... 843 17.4.6.1.4.1.1 Method 1: Bromination of 1H-1-Benzazepines ......................... 843 17.4.6.1.4.1.2 Method 2: Acetylation of 1H-1-Benzazepine ........................... 843 17.4.6.2 2-Benzazepines .......................................................... 844 17.4.6.2.1 Synthesis by Ring-Closure Reactions ....................................... 844 17.4.6.2.1.1 By Formation of One N—C and One C—C Bond ............................. 844 17.4.6.2.1.1.1 Method 1: From (Z)-3-(Tributylstannyl)allylamine and Aryl Bromides ... 844 17.4.6.2.1.1.2 Method 2: From 1,3-Monoazabisylides and Phthalaldehyde ............ 844 17.4.6.2.1.1.3 Method 3: From Cycloaddition of Inden-2-one and 2H-Azirines ......... 845 17.4.6.2.1.2 By Formation of One N—C Bond ........................................... 846 17.4.6.2.1.2.1 Method 1: By Partial Reduction of Acetylenic Benzophenones .......... 846 17.4.6.2.1.3 By Formation of One C—C Bond ........................................... 847 17.4.6.2.1.3.1 Method 1: By Photoisomerization of 3-Phenyl-2-[(Z)-2-phenylvinyl]-2Hazirene ................................................... 847 17.4.6.2.1.3.2 Method 2: By 1,7-Electrocyclization of Diene-Conjugated Nitrile Ylides . 847 17.4.6.2.2 Synthesis by Ring Transformation .......................................... 848 17.4.6.2.2.1 By Ring Enlargement ..................................................... 848 17.4.6.2.2.1.1 Method 1: Base-Mediated Ring Expansion of 1,4-Dihydro-4-(hydroxymethyl)[c]isoquinolines ................................... 848 17.4.6.2.2.1.2 Method 2: By Thermolysis of Dihydrocyclopropa[c]isoquinolines ....... 849 17.4.6.2.2.1.2.1 Variation 1: From 1,4-Dihydro-4-(hydroxymethyl)[c]isoquinolines and Silver(I) Trifluoroacetate ................................... 850 17.4.6.2.2.1.3 Method 3: Deoxygenation of Nitroarenes ............................. 850 17.4.6.2.2.1.4 Method 4: Photolysis of Aryl Azides ................................... 851 17.4.6.2.3 Aromatization ............................................................ 852 17.4.6.2.3.1 Method 1: By syn-Dehydrobromination ............................... 852 17.4.6.2.4 Synthesis by Substituent Modification ..................................... 853 17.4.6.2.4.1 Substitution of Existing Substituents ....................................... 853 17.4.6.2.4.1.1 Of Hydrogen ............................................................. 853 17.4.6.2.4.1.1.1 Method 1: By an Oxygen Functionality ................................ 853 17.4.6.2.4.1.1.2 Method 2: By Tautomerism .......................................... 853 17.4.6.2.4.1.2 Of Heteroatoms .......................................................... 853 17.4.6.2.4.1.2.1 Method 1: Palladium(0)-Catalyzed Carboalkoxylation of 5-Bromo- 5H-2-benzazepines ........................................ 853 17.4.6.2.4.2 Addition Reactions ....................................................... 854 17.4.6.2.4.2.1 Of Hydrogen .......................................................... 854 17.4.6.2.4.2.2 Of Organic Groups ........................................................ 854
Table of Contents XLIX 17.4.6.2.4.2.3 Of Heteroatoms .......................................................... 855 17.4.6.2.4.2.3.1 Method 1: Of Bromine ............................................... 855 17.4.6.2.4.2.3.2 Method 2: N-Oxidation .............................................. 855 17.4.6.2.4.2.3.3 Method 3: Formation of an Annulated Benzazepine ................... 855 17.4.6.3 3H-3-Benzazepines ....................................................... 856 17.4.6.3.1 Synthesis by Ring-Closure Reactions ....................................... 856 17.4.6.3.1.1 By Formation of Two N—C Bonds .......................................... 856 17.4.6.3.1.1.1 Method 1: From 1,2-Phenylenediacetyl Chloride ....................... 856 17.4.6.3.1.2 By Formation of Two C—C Bonds .......................................... 857 17.4.6.3.1.2.1 Method 1: From Phthalaldehyde ...................................... 857 17.4.6.3.1.2.1.1 Variation 1: From 1,2-Dibenzoylbenzene with N,N-Bis(cyanomethyl)isopropylamine .............................................. 857 17.4.6.3.1.3 By Formation of One N—C Bond ........................................... 858 17.4.6.3.1.3.1 Method 1: By Halogen Acid Induced Cyclization of Benzene-1,2diacetonitrile ............................................. 858 17.4.6.3.1.3.2 Method 2: Thermolysis of Vinyl Azides ................................ 858 17.4.6.3.1.4 By Formation of One C—C Bond ........................................... 860 17.4.6.3.1.4.1 Method 1: From Phenylacetimidates .................................. 860 17.4.6.3.1.5 By Annulation to the Heterocyclic Ring .................................... 861 17.4.6.3.1.5.1 Method 1: By [4+2] Cycloaddition of Methyl 2-Pyrone-5-carboxylate with Ethyl 1H-Azepine-1-Carboxylate ....................... 861 17.4.6.3.2 Synthesis by Ring Transformation .......................................... 862 17.4.6.3.2.1 By Ring Enlargement ..................................................... 862 17.4.6.3.2.1.1 Method 1: From 2,3-Benzo-7-azabicyclo[2.2.1]hepta-2,5-dienes ........ 862 17.4.6.3.2.1.2 Method 2: From Azirino[2,1-a]isoquinolines ........................... 862 17.4.6.3.2.1.3 Method 3: From 2-(1a,2,7,7a-Tetrahydro-1H-naphtho[2,3-b]aziren-1-yl)- 1H-isoindole-1,3(2H)-dione ................................ 863 17.4.6.3.3 Aromatization ............................................................ 864 17.4.6.3.3.1 Method 1: By Oxidation (Dehydrogenation) of 7,8-Dimethoxy-5-phenyl- 1,3,4,5-tetrahydro-2H-3-benzazepin-2-one ................. 864 17.4.6.3.4 Synthesis by Substituent Modification ..................................... 864 17.4.6.3.4.1 Substitution of Existing Substituents ....................................... 864 17.4.6.3.4.1.1 Of Hydrogen .............................................................. 864 17.4.6.3.4.1.1.1 Method 1: Nitration of 1H-3-Benzazepin-2-amine ..................... 864 17.4.6.3.4.1.2 Method 2: C1-Methylation of 2,7,8-Trimethoxy-1H-3-benzazepine ...... 865 17.4.6.3.4.2 Of Heteroatoms .......................................................... 865 17.4.6.3.4.2.1 Method 1: Debromination with Palladium on Charcoal ................. 865 17.4.6.3.4.2.2 Method 2: Formation of 2-Ethoxy-7,8-dimethoxy-5-phenyl-1H-3benzazepine .............................................. 866 17.4.6.3.4.2.3 Method 3: By ipso-Substitution of 2-Alkoxy Substituents ............... 866
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 and 38: Table of Contents XLV 17.4.5.1.2.3
Page 39: Table of Contents XLVII 17.4.5.4.1.
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

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