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A new synthesis of pyrroles and porphyrins fused with aromatic rings

DOI: 10.1039/p19960000417

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 417 - 423 (1996)

Update date:2022-08-11

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Authors:

Ono, NoboruOno, Noboru

Hironaga, HideoHironaga, Hideo

Ono, KazuoOno, Kazuo

Kaneko, SyunichiKaneko, Syunichi

Murashima, TakashiMurashima, Takashi

Ueda, TakahiroUeda, Takahiro

Tsukamura, ChikanoriTsukamura, Chikanori

Ogawa, TakujiOgawa, Takuji

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Article abstract of DOI:10.1039/p19960000417

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.

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