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

被引：37

作者：

Taniguchi, S ^{[1
]}

Hasegawa, H

Yanagiya, S

Tabeta, Y

Nakano, Y

Takahashi, M

机构：

[1] Ibaraki Univ, Fac Engn, Dept Mat Sci, Hitachi, Ibaraki 3168511, Japan

[2] Ibaraki Natl Coll Technol, Dept Chem & Mat Engn, Hitachinaka, Ibaraki 3128508, Japan

[3] Ibaraki Univ, Fac Sci, Dept Nat Mat Sci, Mito, Ibaraki 3108512, Japan

来源：

TETRAHEDRON | 2001年 / 57卷 / 11期

关键词：

tripyrrane; porphyrinogen; porphyrin; 21-oxaporphyrinogen; '3+1' type condensation;

D O I：

10.1016/S0040-4020(01)00059-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 state by X-ray crystallography. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：2103 / 2108

页数：6