Selective synthesis of 5-aryl-10-(nitromethyl) substituted 15-azatripyrrane, 15-oxatripyrrane and 15-thiatripyrrane: access to nitromethyl functionalized A 3 B-porphyrins

A chemical strategy toward the selective synthesis of unsymmetrical tripyrranes was developed for the formation of meso -aryl and -nitromethyl substituted A 3 B porphyrins. The iodine catalyzed addition of meso -substituted dipyrromethanes to nitrovinylarenes to generate unsymmetrical 5-aryl-10-(nit...

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Bibliographic Details
Published in:New journal of chemistry 2018, Vol.42 (17), p.14163-14169
Main Authors: Seyitdanlioglu, Pinar, Altundal, Gulberil, Cinar, Seda, Unaleroglu, Canan
Format: Article
Language:English
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Summary:A chemical strategy toward the selective synthesis of unsymmetrical tripyrranes was developed for the formation of meso -aryl and -nitromethyl substituted A 3 B porphyrins. The iodine catalyzed addition of meso -substituted dipyrromethanes to nitrovinylarenes to generate unsymmetrical 5-aryl-10-(nitromethyl) substituted 15-azatripyrranes, 15-oxatripyrranes and 15-thiatripyrrane under mild conditions has been investigated. The multicomponent reactions of 15-azatripyrranes provided the construction of meso -aryl and -nitromethyl substituted A 3 B-porphyrins. To the best of our knowledge, the first examples of 5-aryl-10-(nitromethyl) substituted 15-azatripyrranes, 15-oxatripyrranes and 15-thiatripyrrane, and 5-(nitromethyl)-10,15,20-tris(aryl)porphyrins are introduced in this study.
ISSN:1144-0546
1369-9261
DOI:10.1039/C8NJ01798K