A new synthetic approach to N-arylquinolino[2,3,4-at]porphyrins from beta-arylaminoporphyrins.
A new reaction leading to porphyrins bearing fused rings is described. Novel N-arylquinolino[2,3,4-at]porphyrins 2 were obtained by thermal oxidative cyclization of beta-arylaminoporphyrins 1. The starting beta-arylaminoporphyrins were prepared by two routes: (i) nucleophilic displacement of the nitro group from 2-nitro-5,10,15,20-tetraphenylporphyrin by anilines and (ii) palladium-catalyzed amination of bromobenzene derivatives with (2-amino-5,10,15,20-tetraphenylporphyrinato)nickel(II). The N-arylquinolino[2,3,4-at]porphyrins show interesting UV-vis spectra with strong absorption bands in the red region.
Pereira
Ana M V M
AM
Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal.
Alonso
Cristina M A
CM
Neves
Maria G P M S
MG
Tomé
Augusto C
AC
Silva
Artur M S
AM
Paz
Filipe A A
FA
Cavaleiro
José A S
JA
D018360:Crystallography, X-Ray; D003500:Cyclization; D008958:Models, Molecular; D015394:Molecular Structure; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D011166:Porphyrins; D011804:Quinolines