Direct alkylation of pyrrole with vinyl substituted aromatics: versatile precursors for the synthesis of porphyrinoid macrocycles

Seong Jin Hong, Seung Doo Jeong, Jaeduk Yoo, Jong Seung Kim, Juyoung Yoon, Chang Hee Lee

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12 Scopus citations

Abstract

5-Substituted dipyrromethane analogues (8), (23) and (25) were synthesized by the reaction of 2-vinylpyrroles, 2-vinylthiophene or 2-vinylbenzenes with excess pyrrole in the presence of Lewis acids. Accordingly, tripyrromethane analogues could be obtained by starting with 2,5-divinyl thiophene or 2,6-divinylbenzenes. The reaction usually gave moderate yields and catalyst-dependent was seen in some cases. The reaction is compatible with other reported dipyrromethane syntheses and could be applied for the construction of unusual porphyrins.

Original languageEnglish
Pages (from-to)4138-4141
Number of pages4
JournalTetrahedron Letters
Volume49
Issue number26
DOIs
StatePublished - 23 Jun 2008

Bibliographical note

Funding Information:
This work was supported by a grant from the Korea Science and Engineering Foundation (KOSEF) grant (R01-2006-000-10001-0) funded by the Korean government (MOST). Vascular System Research Center (VSRC) and Central Instrumentation Facility at KNU are acknowledged for support.

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