The synthesis of new tetrabenzo- and tetranaphthoporphyrins via the addition reactions of 4,7-dihydroisoindole

Mikhail A. Filatov; Andrei V. Cheprakov

doi:10.1016/j.tet.2011.01.052

The synthesis of new tetrabenzo- and tetranaphthoporphyrins via the addition reactions of 4,7-dihydroisoindole

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Abstract

The double bond in 4,7-dihydroisoindole derivatives was shown to be a useful reaction site to afford new porphyrinogenic pyrrolic precursors bearing substituted annelated rings via various addition reactions. These precursors are further used to afford new extended porphyrins substituted in the annelated rings. The Sharpless osmium-catalyzed dihydroxylation of dihydroisoindole system was shown to be useful in the synthesis of non-ionogenic water-soluble porphyrin, as well as tetrabenzoporphyrin bearing acetoxy-substituents in benzo-rings. The reverse electron-demand Diels-Alder reaction with tetrachlorothiophene-1,1-dioxide afforded new polychlorosubstituted tetranaphthoporphyrin.

Original language	English
Pages (from-to)	3559-3566
Number of pages	8
Journal	Tetrahedron
Volume	67
Issue number	19
DOIs	https://doi.org/10.1016/j.tet.2011.01.052
Publication status	Published - 13 May 2011
Externally published	Yes

Keywords

Inverse electron demand Diels-Alder reaction
NIR optical materials
Tetrabenzoporphyrin
Tetranaphthoporphyrin
Water-soluble porphyrins

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10.1016/j.tet.2011.01.052

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title = "The synthesis of new tetrabenzo- and tetranaphthoporphyrins via the addition reactions of 4,7-dihydroisoindole",

abstract = "The double bond in 4,7-dihydroisoindole derivatives was shown to be a useful reaction site to afford new porphyrinogenic pyrrolic precursors bearing substituted annelated rings via various addition reactions. These precursors are further used to afford new extended porphyrins substituted in the annelated rings. The Sharpless osmium-catalyzed dihydroxylation of dihydroisoindole system was shown to be useful in the synthesis of non-ionogenic water-soluble porphyrin, as well as tetrabenzoporphyrin bearing acetoxy-substituents in benzo-rings. The reverse electron-demand Diels-Alder reaction with tetrachlorothiophene-1,1-dioxide afforded new polychlorosubstituted tetranaphthoporphyrin.",

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AU - Filatov, Mikhail A.

AU - Cheprakov, Andrei V.

PY - 2011/5/13

Y1 - 2011/5/13

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AB - The double bond in 4,7-dihydroisoindole derivatives was shown to be a useful reaction site to afford new porphyrinogenic pyrrolic precursors bearing substituted annelated rings via various addition reactions. These precursors are further used to afford new extended porphyrins substituted in the annelated rings. The Sharpless osmium-catalyzed dihydroxylation of dihydroisoindole system was shown to be useful in the synthesis of non-ionogenic water-soluble porphyrin, as well as tetrabenzoporphyrin bearing acetoxy-substituents in benzo-rings. The reverse electron-demand Diels-Alder reaction with tetrachlorothiophene-1,1-dioxide afforded new polychlorosubstituted tetranaphthoporphyrin.

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KW - Tetrabenzoporphyrin

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The synthesis of new tetrabenzo- and tetranaphthoporphyrins via the addition reactions of 4,7-dihydroisoindole

Abstract

Keywords

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