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

17.7.4.1.1.1.2 Method 2: Reaction <strong>of</strong> Cyclopenta[c]quinolizine with Dimethyl<br />

Acetylenedicarboxylate ................................... 1058<br />

17.7.4.1.2 Synthesis by Ring Transformation ......................................... 1059<br />

17.7.4.1.2.1 Method 1: Using Diels–Alder Reaction <strong>of</strong> Acetylenedicarboxylate ..... 1059<br />

17.7.4.1.3 Synthesis by Substituent Modification .................................... 1059<br />

17.7.4.1.3.1 Substitution <strong>of</strong> Existing Substituents ...................................... 1059<br />

17.7.4.1.3.1.1 Of Hydrogen ............................................................. 1059<br />

17.7.4.1.3.1.1.1 Method 1: Nitration Using Copper(II) Nitrate ......................... 1059<br />

17.7.4.1.3.1.2 Of Carbon Functionalities ................................................ 1060<br />

17.7.4.1.3.1.2.1 Method 1: Thermolysis <strong>of</strong> a Pyrido[2,1,6- de]quinolizine-4,5dicarboxylate<br />

............................................ 1060<br />

17.7.4.1.3.1.2.2 Method 2: Decarboxylation <strong>of</strong> Dimethyl Cyclopenta[ij]pyrido[2,1,6-de]quinolizine-4,5-dicarboxylate<br />

................. 1061<br />

17.7.4.2 Aza- and Polyaza[3.3.3]cyclazines ........................................ 1061<br />

17.7.4.2.1 Synthesis by Ring-Closure Reactions ...................................... 1062<br />

17.7.4.2.1.1 By Formation <strong>of</strong> Three N—C Bonds ........................................ 1062<br />

17.7.4.2.1.1.1 Method 1: By Using Ethoxymethylene Compounds ................... 1062<br />

17.7.4.2.1.1.1.1 Variation 1: By Using Methoxymethylene Compounds ................. 1063<br />

17.7.4.2.1.1.2 Method 2: By Condensation with Acid Anhydrides .................... 1064<br />

17.7.4.2.1.2 By Formation <strong>of</strong> One N—C and Two C—C Bonds ............................ 1064<br />

17.7.4.2.1.2.1 Method 1: By Using Ethoxymethylene Compounds ................... 1064<br />

17.7.4.2.1.3 By Formation <strong>of</strong> One N—C and One C—C Bond ............................ 1065<br />

17.7.4.2.1.3.1 Method 1: By Condensation with Acid Anhydrides .................... 1065<br />

17.7.4.2.1.3.2 Method 2: By Condensation <strong>of</strong> a Dihydro-4H-quinolizin-4-imine with<br />

an Acid Anhydride ....................................... 1066<br />

17.7.4.2.1.4 By Formation <strong>of</strong> Two C—C Bonds ......................................... 1066<br />

17.7.4.2.1.4.1 Method 1: Cycloaddition <strong>of</strong> Imino Compounds with Dimethyl<br />

Acetylenedicarboxylate ................................... 1066<br />

17.7.4.2.2 Synthesis by Ring Transformation ......................................... 1067<br />

17.7.4.2.2.1 Method 1: Using Diels–Alder Reaction <strong>of</strong> Dimethyl<br />

Acetylenedicarboxylate ................................... 1067<br />

17.7.4.2.2.2 Method 2: By Dehydrogenation Using Palladium on Carbon ........... 1068<br />

17.7.5 Product Subclass 5: [2.2.4]Cyclazines (Azepino[2,1,7-cd]pyrrolizines) ... 1069<br />

17.7.5.1 Synthesis by Ring-Closure Reactions ...................................... 1069<br />

17.7.5.1.1 By Formation <strong>of</strong> Two C—C Bonds ......................................... 1069<br />

17.7.5.1.1.1 Method 1: Reaction <strong>of</strong> a Saturated Compound with a Perchlorate ..... 1069<br />

17.7.5.1.2 Synthesis by Substituent Modification .................................... 1070<br />

17.7.5.1.2.1 Substitution <strong>of</strong> Existing Substituents ...................................... 1070<br />

17.7.5.1.2.1.1 Of Hydrogen ............................................................. 1070

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