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ISSN 1998-9539

A Versatile General Approach to the Synthesis of Linearly Annelated π-Extended Porphyrins via 4,7-Dihydroisoindole Derivatives

Mikhail A. Filatov, Sergei E. Aleshchenkov, and Andrei V. Cheprakov@


Department of Chemistry, Moscow State University, Moscow, 119992, Russia


@Corresponding author E-mail: avchep@elorg.chem.msu.ru


A convenient and straightforward approach to the synthesis of linearly annelated extended porphyrins of tetrabenzo- and tetranaphthoporphyrin series was developed. 4,7-Dihydroisoindole and its benzoannelated derivative, being the closest stable precursors of unstable 2H-isoinsoles, are used in this method. Key features for this approach are its unprecedented synthetic versatility, tolerance for sensitive functional groups and the convenient introduction of meso-substituents. Aromatization of the annelated rings is conducted under mild conditions at the final stage of the synthesis. Tetraaryltetrabenzo- and tetranaphthoporphyrins are obtained using standard well-established procedures of porphyrin synthesis using common synthons.

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