A new synthesis of pyrroles and porphyrins fused with aromatic rings

被引:90
作者
Ono, N
Hironaga, H
Ono, K
Kaneko, S
Murashima, T
Ueda, T
Tsukamura, C
Ogawa, T
机构
[1] Department of Chemistry, Faculty of Science, Ehime University
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1996年 / 05期
关键词
D O I
10.1039/p19960000417
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Pyrroles fused with aromatic rings (isoindole derivatives) have been readily prepared by the reaction of aromatic nitro compounds with ethyl isocyanoacetate in the presence of DBU. The ease of this reaction depends on the aromaticity of the starting nitro aromatics. Polycyclic aromatic nitro compounds such as 1-nitroacenaphthylene or 9-nitrophenanthrene are more reactive than simple nitro aromatics such as nitrobenzene or nitronaphthalenes and give the corresponding pyrroles in good yields. Pyrroles prepared by this method have been converted into porphyrins fused with various aromatic rings by the reduction with LiAlH4 followed by treatment with an acid catalyst and oxidation with chloranil or oxygen. Tetra-1,2-naphthoporphyrin has been prepared by the reaction of 2-nitro-3,4-dihydronaphthalene or 1-nitronaphthalene with ethyl isocyanoacetate followed by reduction, tetramerization and oxidation. Thus, highly conjugated porphyrins are readily prepared starting from aromatic nitro compounds, and their electronic and optical properties can be controlled by choice of the starting aromatic nitro compound.
引用
收藏
页码:417 / 423
页数:7
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