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

abstract

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.

keywords

SUBSTITUTED-MESO-TETRAPHENYLPORPHYRINS; PORPHYRIN-PHTHALOCYANINE DYADS; CHIRAL PORPHYRINS; EFFICIENT SYNTHESIS; AMINATION; METALLO-2-NITRO-5,10,15,20-TETRAPHENYLPORPHYRINS; CYCLOPROPANATION; BROMOPORPHYRINS; AMIDATION; ION

subject category

Chemistry

authors

Pereira, AMVM; Alonso, CMA; Neves, MGPMS; Tome, AC; Silva, AMS; Paz, FAA; Cavaleiro, JAS

our authors

acknowledgements

Thanks are due to Fundacao para a Ciencia e a Tecnologia (FCT, Portugal) and POCI 2010 (FEDER) for funding the Organic Chemistry Research Unit and C the purchase of the single-crystal diffractometer. A.M.V.M.P. and C.M.A.A. also thank FCT for their SFRH/BD/22691/2005 and SFRH/BPD/8375/2002 grants, respectively.

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