Preparation of Highly Conjugated Oligoaza-PAHs Based on the Oxidative Intramolecular Coupling of Bicyclo[2.2.2]octadiene-Fused Pyrrole

Abstract

The substitution reactions of tetrafluoro-p-phthalonitrile and hexafluorobenzene with 4,7-dihydro-4,7-ethano-2H-isoindole under basic conditions afforded tetra(4,7-dihydro-4,7-ethano-2H-isoindol-2-yl)-substituted p-phthalonitrile and 1,4-difluorobenzene in good yields, respectively. Oxidative coupling reactions of these compounds gave tetra(bicycle[2.2.2]octadiene)-fused tetrapyrrolo[1,2-a;1',2'-c;1'',2''h;1''',2'''-j][1,4,5,8]tetraazaanthracenes, which were then converted to tetraisoindolo[1,2-a;1',2'-c;1'',2''-h;1''',2'''-j]-[1,4,5,8]tetraazaanthracenes by the retro-Diels-Alder reaction.

Keywords

ChemistryIntramolecular forceBicyclic moleculeConjugated systemOxidative coupling of methanePyrroleOxidative phosphorylationCoupling (piping)Organic chemistryCombinatorial chemistryMedicinal chemistryCatalysis

MeSH Terms

AnimalsChickensPhenotypeFracturesBoneFemaleBone and BonesPolymorphismSingle NucleotideRadiographyGenotype

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Publication Info

Year: 2010
Type: article
Volume: 82
Issue: 1
Pages: 791-791
Citations: 7
Access: Closed

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APA Style

                            
                                
                                    Hidemitsu Uno, 
                                
                                    Takahiro Takiue, 
                                
                                    H. Uoyama
                                
                                et al.
                            
                            (2010). 
                            Preparation of Highly Conjugated Oligoaza-PAHs Based on the Oxidative Intramolecular Coupling of Bicyclo[2.2.2]octadiene-Fused Pyrrole. 
                            Heterocycles
                            , 82
                            (1)
                            , 791-791.
                            https://doi.org/10.3987/com-10-s(e)69
                        

Identifiers

DOI: 10.3987/com-10-s(e)69
PMID: 41310424
PMCID: PMC12661725

Data Quality

Data completeness: 86%