4.7 Article

A new synthetic approach to N-arylquinolino[2,3,4-at]porphyrins from β-arylaminoporphyrins

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 73, Issue 18, Pages 7353-7356

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo800975c

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Funding

  1. Fundacao para a Ciencia e a Tecnologia (FCT, Portugal) [SFRH/BD/22691/2005, SFRH/BPD/8375/2002]
  2. FEDER [POCI 2010]
  3. Fundação para a Ciência e a Tecnologia [SFRH/BPD/8375/2002, SFRH/BD/22691/2005] Funding Source: FCT

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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.

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