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LVI Table of Contents
17.6 Product Class 6: Eight- and Nine-Membered Hetarenes and
Heteroannulenes with One or More Heteroatoms
R. M. Borzilleri
17.6 Product Class 6: Eight- and Nine-Membered Hetarenes and
Heteroannulenes with One or More Heteroatoms ....................... 979
17.6.1 Product Subclass 1: Azocines ............................................ 979
17.6.1.1 Synthesis by Ring Transformation .......................................... 979
17.6.1.1.1 Valence Isomerization .................................................... 980
17.6.1.1.1.1 Method 1: From 2-Azabicyclo[4.2.0]octa-2,4,7-triene via
Diazabasketene ........................................... 980
17.6.1.1.1.2 Method 2: From Substituted Methoxyazabicyclo[4.2.0]octa-3,7-dienes . 980
17.6.1.1.1.3 Method 3: Photocycloaddition of Benzonitriles and Phenols ............ 981
17.6.1.1.1.4 Method 4: Cycloaddition of 2-Phenylbenzazetes ....................... 983
17.6.1.1.1.5 Method 5: Photocyclodimerization of Pyridines ....................... 983
17.6.1.1.1.6 Method 6: Thermolysis of Tricyclo[4.2.2.0 2,5 ]deca-3,7,9-trienes and
1,2,4-Triazines ............................................ 984
17.6.1.1.2 By Rearrangement ........................................................ 985
17.6.1.1.2.1 Method 1: Of Benzocycloheptatriene Azides .......................... 985
17.6.1.2 Aromatization .......................................................... 986
17.6.1.2.1 Method 1: Bromination/Dehydrobromination of Dihydroazocines ...... 986
17.6.1.3 Synthesis by Substituent Modification ..................................... 987
17.6.1.3.1 Modification of Substituents .............................................. 987
17.6.1.3.1.1 Method 1: O-Methylation of Dihydroazocinones with Meerwein s
Reagent .................................................. 987
17.6.2 Product Subclass 2: Diazocines and Diheterocines ....................... 988
17.6.2.1 Synthesis by Ring-Closure Reactions ....................................... 989
17.6.2.1.1 By Formation of Two N—C Bonds .......................................... 989
17.6.2.1.1.1 Method 1: 1,2-Diazocines by Condensation of Biphenyl Dicarbonyl
Compounds with Hydrazines .............................. 989
17.6.2.1.1.2 Method 2: 1,4-Diazocines by Condensations of Diones with Diamines .. 990
17.6.2.1.1.2.1 Variation 1: Condensations of 1,2-Diones with Biphenyl-2,2¢-diamines ... 990
17.6.2.1.1.2.2 Variation 2: By Condensations of 1,4-Diones with Benzene-1,2-diamines . 991
17.6.2.1.1.3 Method 3: Annulated 1,5-Diazocines by Self-Condensation of
2-(Trimethoxymethyl)aniline ............................... 992
17.6.2.1.1.4 Method 4: 1,5-Diazocines by Bimolecular Condensation of
2-Aminobenzophenones .................................. 992
17.6.2.1.1.4.1 Variation 1: From the Acid-Catalyzed Intermolecular Condensation of
2-Aminobenzophenones .................................. 992
17.6.2.1.1.4.2 Variation 2: Condensation of 2-Aminobenzophenones or 2-Aminothiobenzophenones
Derived from Benz[c]isoxazoles or
Benz[c]isothiazoles ........................................ 993