A New Synthetic Approach to N-Arylquinolino[2,3,4-at]porphyrins from β-Arylaminoporphyrins
- 22 August 2008
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 73 (18) , 7353-7356
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 β-arylaminoporphyrins 1. The starting β-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
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