Issue 8, 1994

New syntheses of biliverdins, corroles and azaporphyrins from 1,19-dibromo-ac-biladiene salts

Abstract

Treatment of the readily available, 1,19 dibromo-ac-biladiene dihydrobromide salts 3 with dimethyl sulfoxide (DMSO) in presence of a catalytic amount of toluene-p-sulfonic acid affords symmetrical and unsymmetrical biliverdins 4 in excellent yield; unsymmetrically substituted 1,19 dibromo-ac-biladiene dihydrobromide 3c was prepared in a stepwise fashion via a tripyrrin salt. Under appropriate reaction conditions, the ac-biladiene dihydrobromides were also converted in modest yields into the corroles 5 and the azaporphyrins 6.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1994, 971-977

New syntheses of biliverdins, corroles and azaporphyrins from 1,19-dibromo-ac-biladiene salts

R. K. Pandey, K. R. Gerzevske, H. Zhou and K. M. Smith, J. Chem. Soc., Perkin Trans. 1, 1994, 971 DOI: 10.1039/P19940000971

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