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

doi:10.1016/j.tetlet.2008.04.119

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

Research output: Contribution to journal › Article › peer-review

12 Citations (Scopus)

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 language	English
Pages (from-to)	4138-4141
Number of pages	4
Journal	Tetrahedron Letters
Volume	49
Issue number	26
DOIs	https://doi.org/10.1016/j.tetlet.2008.04.119
Publication status	Published - 2008 Jun 23

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.

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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

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.",

author = "Hong, {Seong Jin} and Jeong, {Seung Doo} and Jaeduk Yoo and Kim, {Jong Seung} and Juyoung Yoon and Lee, {Chang Hee}",

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AU - Jeong, Seung Doo

AU - Yoo, Jaeduk

AU - Kim, Jong Seung

AU - Yoon, Juyoung

AU - Lee, Chang Hee

N1 - 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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N2 - 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.

AB - 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.

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

Abstract

Bibliographical note

ASJC Scopus subject areas

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