Organic & biomolecular chemistry

Oligocyclization of 2-(hydroxymethyl) pyrroles with electron-withdrawing groups at β-positions: formation and structural elucidation of porphyrinogens and …

H Uno, K Inoue, T Inoue, N Ono

Index: Uno, Hidemitsu; Inoue, Kentarou; Inoue, Takashi; Ono, Noboru Organic and Biomolecular Chemistry, 2003 , vol. 1, # 21 p. 3857 - 3865

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Citation Number: 18

Abstract

Acid-catalyzed oligomerization of 2-(hydroxymethyl) pyrroles bearing C6F5, 2, 6-Cl2C6H3, CF3 and CO2Et groups at β-positions was examined. The reaction of ethyl pyrrole-3- carboxylates gave a mixture of oligomers and type I isomers of porphyrinogens and hexaphyrinogens were isolated when the other β-substituents were sufficiently bulky, for example, mesityl, 2, 6-Cl2C6H3 and C6F5 groups. On the other hand, the pyrroles having ...