Skeletal Rearrangement of Twisted Thia-Norhexaphyrin: Multiply Annulated Polypyrrolic Aromatic Macrocycles

Qizhao Li, Masatoshi Ishida, Hiroto Kai, Tingting Gu, Chengjie Li, Xin Li, Glib Baryshnikov, Xu Liang, Weihua Zhu, Hans Ågren, Hiroyuki Furuta, Yongshu Xie

研究成果: ジャーナルへの寄稿学術誌査読

18 被引用数 (Scopus)

抄録

A hybrid thia-norhexaphyrin comprising a directly linked N-confused pyrrole and thiophene unit (1) revealed unique macrocycle transformations to afford multiply inner-annulated aromatic macrocycles. Oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone triggered a cleavage of the C-S bond of the thiophene unit, accompanied with skeletal rearrangement to afford unique π-conjugated products: a thiopyrrolo-pentaphyrin embedded with a pyrrolo[1,2]isothiazole (2), a sulfur-free pentaphyrin incorporating an indolizine moiety (3), and a thiopyranyltriphyrinoid containing a 2H-thiopyran unit (4). Furthermore, 2 underwent desulfurization reactions to afford a fused pentaphyrin containing a pyrrolizine moiety (5) under mild conditions. Using expanded porphyrin scaffolds, oxidative thiophene cleavage and desulfurization of the hitherto unknown N-confused core-modified macrocycles would be a practical approach for developing unique polypyrrolic aromatic macrocycles.

本文言語英語
ジャーナルAngewandte Chemie - International Edition
DOI
出版ステータス印刷前の電子出版 - 3月 7 2019

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