Tetrahedron

The first isolation of unsubstituted porphyrinogen and unsubstituted 21-oxaporphyrinogen by the '3+ 1'approach from 2, 5-bis (hydroxymethyl) pyrrole and tripyrrane …

S Taniguchi, H Hasegawa, S Yanagiya, Y Tabeta…

Index: Taniguchi, Shozo; Hasegawa, Hikaru; Yanagiya, Shoko; Tabeta, Yusuke; Nakano, Yoshiharu; Takahashi, Masahiko Tetrahedron, 2001 , vol. 57, # 11 p. 2103 - 2108

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Citation Number: 29

Abstract

The treatment of 2, 5-bis (hydroxymethyl) pyrrole or 2, 5-bis (hydroxymethyl) furan with pyrrole in the presence of hydrochloric acid gave tripyrrane and 2, 5-bis (2-pyrrolylmethyl) furan in 58–61% yield, which afforded the simplest porphyrinogen (hexahydroporphine) and 21-oxaporphyrinogen by the '3+ 1'approach in 14 and 11% yields, respectively. 21- Oxaporphyrinogen has been shown to adopt a 1, 2-alternated conformation in the solid ...