3,4-Dialkoxypyrroles and 2,3,7,8,12,13,17,18-Octaalkoxyporphyrins

Andreas Merz; Roland Schropp; Eleonore Dötterl

doi:10.1055/s-1995-3993

Synthesis 1995; 1995(7): 795-800
DOI: 10.1055/s-1995-3993

paper

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3,4-Dialkoxypyrroles and 2,3,7,8,12,13,17,18-Octaalkoxyporphyrins

Andreas Merz^* , Roland Schropp, Eleonore Dötterl

^*Institut für Organische Chemie, Universität Regensburg, D-93040 Regensburg, Germany, Fax +49(941)9434505; E-mail Andreas.Merz@chemie.uni-regensburg.de

Abstract

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A five-step general synthesis of 3,4-dialkoxypyrroles 7c-f is described starting with the condensation of dimethyl N-benzyliminodiacetate (1b) and diethyl oxalate to give dimethyl 1-benzyl-3,4-dihydroxypyrrole-2,5-dicarboxylate (2b), which is bis-O-alkylated to the corresponding 3,4-diethers 3c-g. Pyrrole N-benzyl cleavage followed by ester hydrolysis and decarboxylation leads to 7c-f in 10-50% overall yield. Pyrroles 7c-f react with formaldehyde or benzaldehydes to give meso-H- (8a-d) or meso-tetraaryloctaalkoxyporphyrins 9a-g in moderate yields.

O-alkylation of dihydroxypyrroles - N-benzyl protective group - decarboxylation - Fischer-Rothemund porphyrin synthesis

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