Toward carboxylate group functionalized A4, A2B 2, A3B oxaporphyrins and zinc complex of oxaporphyrins

Ram Ambre; Chien Yi Yu; Sandeep B. Mane; Ching Fa Yao; Chen Hsiung Hung

doi:10.1016/j.tet.2011.04.034

Toward carboxylate group functionalized A₄, A₂B ₂, A₃B oxaporphyrins and zinc complex of oxaporphyrins

Ram Ambre, Chien Yi Yu, Sandeep B. Mane, Ching Fa Yao, Chen Hsiung Hung^*

^*Corresponding author for this work

Department of Chemistry

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

16 Citations (Scopus)

Abstract

Series of new oxaporphyrins were isolated from the reaction of furan-1,4-diol, pyrrole, and an aldehyde under Lindsey's conditions, which gives easy access to ester group functionalized oxaporphyrins. The ester substituents can be readily hydrolyzed to terminal carboxylic acid in the presence of KOH. The Zn(II) oxaporphyrins have been synthesized from the reaction of free base with ZnCl₂ and fully characterized by variable temperature NMR, 2D NMR, and single crystal X-ray diffraction studies.

Original language	English
Pages (from-to)	4680-4688
Number of pages	9
Journal	Tetrahedron
Volume	67
Issue number	25
DOIs	https://doi.org/10.1016/j.tet.2011.04.034
Publication status	Published - 2011 Jun 24

Keywords

Core-Modified Porphyrin
Oxaporphyrin
Porphyrin Synthesis
X-ray structure
Zinc Porphyrin

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tet.2011.04.034

Cite this

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title = "Toward carboxylate group functionalized A4, A2B 2, A3B oxaporphyrins and zinc complex of oxaporphyrins",

abstract = "Series of new oxaporphyrins were isolated from the reaction of furan-1,4-diol, pyrrole, and an aldehyde under Lindsey's conditions, which gives easy access to ester group functionalized oxaporphyrins. The ester substituents can be readily hydrolyzed to terminal carboxylic acid in the presence of KOH. The Zn(II) oxaporphyrins have been synthesized from the reaction of free base with ZnCl2 and fully characterized by variable temperature NMR, 2D NMR, and single crystal X-ray diffraction studies.",

keywords = "Core-Modified Porphyrin, Oxaporphyrin, Porphyrin Synthesis, X-ray structure, Zinc Porphyrin",

author = "Ram Ambre and Yu, {Chien Yi} and Mane, {Sandeep B.} and Yao, {Ching Fa} and Hung, {Chen Hsiung}",

year = "2011",

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day = "24",

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language = "English",

volume = "67",

pages = "4680--4688",

journal = "Tetrahedron",

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T1 - Toward carboxylate group functionalized A4, A2B 2, A3B oxaporphyrins and zinc complex of oxaporphyrins

AU - Ambre, Ram

AU - Yu, Chien Yi

AU - Mane, Sandeep B.

AU - Yao, Ching Fa

AU - Hung, Chen Hsiung

PY - 2011/6/24

Y1 - 2011/6/24

N2 - Series of new oxaporphyrins were isolated from the reaction of furan-1,4-diol, pyrrole, and an aldehyde under Lindsey's conditions, which gives easy access to ester group functionalized oxaporphyrins. The ester substituents can be readily hydrolyzed to terminal carboxylic acid in the presence of KOH. The Zn(II) oxaporphyrins have been synthesized from the reaction of free base with ZnCl2 and fully characterized by variable temperature NMR, 2D NMR, and single crystal X-ray diffraction studies.

AB - Series of new oxaporphyrins were isolated from the reaction of furan-1,4-diol, pyrrole, and an aldehyde under Lindsey's conditions, which gives easy access to ester group functionalized oxaporphyrins. The ester substituents can be readily hydrolyzed to terminal carboxylic acid in the presence of KOH. The Zn(II) oxaporphyrins have been synthesized from the reaction of free base with ZnCl2 and fully characterized by variable temperature NMR, 2D NMR, and single crystal X-ray diffraction studies.

KW - Core-Modified Porphyrin

KW - Oxaporphyrin

KW - Porphyrin Synthesis

KW - X-ray structure

KW - Zinc Porphyrin

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U2 - 10.1016/j.tet.2011.04.034

DO - 10.1016/j.tet.2011.04.034

M3 - Article

AN - SCOPUS:79957770501

SN - 0040-4020

VL - 67

SP - 4680

EP - 4688

JO - Tetrahedron

JF - Tetrahedron

IS - 25

ER -

Toward carboxylate group functionalized A₄, A₂B ₂, A₃B oxaporphyrins and zinc complex of oxaporphyrins

Abstract

Keywords

ASJC Scopus subject areas

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CCDC 809694: Experimental Crystal Structure Determination

Cite this

Toward carboxylate group functionalized A4, A2B 2, A3B oxaporphyrins and zinc complex of oxaporphyrins

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 809694: Experimental Crystal Structure Determination

Cite this

Toward carboxylate group functionalized A₄, A₂B ₂, A₃B oxaporphyrins and zinc complex of oxaporphyrins