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LXII Table of Contents 17.7.4.1.1.1.2 Method 2: Reaction of Cyclopenta[c]quinolizine with Dimethyl Acetylenedicarboxylate ................................... 1058 17.7.4.1.2 Synthesis by Ring Transformation ......................................... 1059 17.7.4.1.2.1 Method 1: Using Diels–Alder Reaction of Acetylenedicarboxylate ..... 1059 17.7.4.1.3 Synthesis by Substituent Modification .................................... 1059 17.7.4.1.3.1 Substitution of Existing Substituents ...................................... 1059 17.7.4.1.3.1.1 Of Hydrogen ............................................................. 1059 17.7.4.1.3.1.1.1 Method 1: Nitration Using Copper(II) Nitrate ......................... 1059 17.7.4.1.3.1.2 Of Carbon Functionalities ................................................ 1060 17.7.4.1.3.1.2.1 Method 1: Thermolysis of a Pyrido[2,1,6- de]quinolizine-4,5dicarboxylate ............................................ 1060 17.7.4.1.3.1.2.2 Method 2: Decarboxylation of Dimethyl Cyclopenta[ij]pyrido[2,1,6-de]quinolizine-4,5-dicarboxylate ................. 1061 17.7.4.2 Aza- and Polyaza[3.3.3]cyclazines ........................................ 1061 17.7.4.2.1 Synthesis by Ring-Closure Reactions ...................................... 1062 17.7.4.2.1.1 By Formation of Three N—C Bonds ........................................ 1062 17.7.4.2.1.1.1 Method 1: By Using Ethoxymethylene Compounds ................... 1062 17.7.4.2.1.1.1.1 Variation 1: By Using Methoxymethylene Compounds ................. 1063 17.7.4.2.1.1.2 Method 2: By Condensation with Acid Anhydrides .................... 1064 17.7.4.2.1.2 By Formation of One N—C and Two C—C Bonds ............................ 1064 17.7.4.2.1.2.1 Method 1: By Using Ethoxymethylene Compounds ................... 1064 17.7.4.2.1.3 By Formation of One N—C and One C—C Bond ............................ 1065 17.7.4.2.1.3.1 Method 1: By Condensation with Acid Anhydrides .................... 1065 17.7.4.2.1.3.2 Method 2: By Condensation of a Dihydro-4H-quinolizin-4-imine with an Acid Anhydride ....................................... 1066 17.7.4.2.1.4 By Formation of Two C—C Bonds ......................................... 1066 17.7.4.2.1.4.1 Method 1: Cycloaddition of Imino Compounds with Dimethyl Acetylenedicarboxylate ................................... 1066 17.7.4.2.2 Synthesis by Ring Transformation ......................................... 1067 17.7.4.2.2.1 Method 1: Using Diels–Alder Reaction of Dimethyl Acetylenedicarboxylate ................................... 1067 17.7.4.2.2.2 Method 2: By Dehydrogenation Using Palladium on Carbon ........... 1068 17.7.5 Product Subclass 5: [2.2.4]Cyclazines (Azepino[2,1,7-cd]pyrrolizines) ... 1069 17.7.5.1 Synthesis by Ring-Closure Reactions ...................................... 1069 17.7.5.1.1 By Formation of Two C—C Bonds ......................................... 1069 17.7.5.1.1.1 Method 1: Reaction of a Saturated Compound with a Perchlorate ..... 1069 17.7.5.1.2 Synthesis by Substituent Modification .................................... 1070 17.7.5.1.2.1 Substitution of Existing Substituents ...................................... 1070 17.7.5.1.2.1.1 Of Hydrogen ............................................................. 1070
Table of Contents LXIII 17.7.5.1.2.1.1.1 Method 1: The Vilsmeier Reaction of a [2.2.4]Cyclazine with Dimethylformamide ...................................... 1070 17.7.5.1.2.1.1.2 Method 2: Nitration with Tetranitromethane ......................... 1071 17.7.6 Product Subclass 6: [2.3.4]Cyclazines (Azepino[2,1,7-cd]indolizines) .... 1071 17.7.6.1 Synthesis by Ring-Closure Reactions ...................................... 1072 17.7.6.1.1 By Formation of Two C—C Bonds ......................................... 1072 17.7.6.1.1.1 Method 1: Wittig Reaction of an Aldehyde Followed by Intramolecular Cyclization of an Oxo Diester ............................. 1072 17.7.7 Product Subclass 7: Annulenes Bridged byTwo Nitrogen Atoms ........ 1072 17.7.7.1 Aromatization ......................................................... 1073 17.7.7.1.1 Method 1: From 3,4,7,8-Tetrahydro-8b,8c-diazacyclopenta[fg]acenaphthylene ............................................. 1073 17.8 Product Class 8: Porphyrins and Related Compounds K. M. Smith and M. G. H. Vicente 17.8 Product Class 8: Porphyrins and Related Compounds ................... 1081 17.8.1 Product Subclass 1: Porphyrins ......................................... 1085 17.8.1.1 Syntheses of Intermediates Used in Porphyrin Syntheses ................... 1087 17.8.1.1.1 Dipyrroles ............................................................... 1088 17.8.1.1.1.1 Method 1: Dipyrromethenes ........................................ 1088 17.8.1.1.1.1.1 Variation 1: Condensation of 2-Formyl-1H-pyrroles with 2-Unsubstituted 1H-Pyrroles .............................................. 1088 17.8.1.1.1.1.2 Variation 2: Reaction of 2-(Bromomethyl)-1H-pyrroles with 2-Bromo-1H-pyrroles ..................................... 1089 17.8.1.1.1.1.3 Variation 3: Self-Condensation of Monopyrroles ....................... 1090 17.8.1.1.1.1.4 Variation 4: Oxidation of Dipyrromethanes ............................ 1091 17.8.1.1.1.2 Method 2: Dipyrromethanes ........................................ 1091 17.8.1.1.1.2.1 Variation 1: Unsymmetrically Substituted Dipyrromethanes by Reaction of 2-Substituted 1H-Pyrroles with 2-Unsubstituted 1H-Pyrroles .............................................. 1091 17.8.1.1.1.2.2 Variation 2: Unsymmetrically Substituted Dipyrromethanes by Reduction of Dipyrromethenes ........................... 1093 17.8.1.1.1.2.3 Variation 3: Symmetrically Substituted Dipyrromethanes by Self-Condensation of 2-Substituted 1H-Pyrroles ............ 1094 17.8.1.1.1.2.4 Variation 4: Symmetrically Substituted Dipyrromethanes from 2-Unsubstituted 1H-Pyrroles .............................. 1095 17.8.1.1.1.3 Method 3: Dipyrroketones .......................................... 1096 17.8.1.1.1.4 Method 4: Bipyrroles ................................................ 1098 17.8.1.1.2 Tripyrroles ............................................................... 1100 17.8.1.1.2.1 Method 1: The [2 +1] Approach to Tripyrranes ........................ 1100 17.8.1.1.2.2 Method 2: The [1]+[1] 2 Approach to Symmetrical Tripyrranes ......... 1102 17.8.1.1.3 Open-Chain Tetrapyrrolic Intermediates ................................... 1103
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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 and 40: Table of Contents XLVII 17.4.5.4.1.
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: Table of Contents LXI 17.7.3.2 [2.3
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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