Pictet-Spengler Synthesis of N-Heteroaromatics Extended Porphyrins.

IF 1.7 4区化学 Q3 CHEMISTRY, ORGANIC Current organic synthesis Pub Date : 2023-07-12 DOI:10.2174/1570179420666230712155402

Dileep Kumar Singh

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Abstract

Background: Porphyrins are highly conjugated heterocyclic compounds and are found as the backbone of many natural products such as heme and chlorophyll. To improve its biological and optical properties, the functionalization of porphyrin at its β- and meso-position has gained importance in recent years.

Objective: The purpose of this review is to describe the Pictet-Spengler method for the incorporation of nitrogenous and biologically important heterocyclic scaffolds such as pyrrolo-/indolo[1,2-a]quinoxaline, pyrrolo[1,2-a]pyrazine, and quinoline at the β- and meso-positions of the porphyrins to increase π-conjugation and improve their biological, optical, and electrochemical properties.

Conclusion: This review provides a comprehensive overview of the synthesis of N-heterocyclic extended porphyrins and metalloporphyrins via a modified Pictet-Spengler approach. The synthesized porphyrins were found to be highly conjugated and exhibited improved photophysical properties compared to their parent analogues. Moreover, the review article provided a brief overview of the Pictet-Spengler procedure, including product yields, reaction conditions, photophysical properties of the synthesized products, and potential applications in a variety of fields.

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n -杂芳烃扩展卟啉的Pictet-Spengler合成。

背景:卟啉是一种高度共轭的杂环化合物，是许多天然产物如血红素和叶绿素的主干。为了提高卟啉的生物学和光学性能，近年来研究卟啉β位和介位的功能化具有重要意义。目的:利用picet - spengler方法在卟啉类化合物的β位和介位上引入吡咯-/吲哚[1,2-a]喹啉、吡咯[1,2-a]吡嗪和喹啉等具有重要生物学意义的含氮杂环支架，以提高其π共轭性，改善其生物学、光学和电化学性能。结论:本文综述了利用改进的Pictet-Spengler方法合成n -杂环扩展卟啉和金属卟啉的研究进展。结果表明，合成的卟啉具有高度共轭性，其光物理性质比亲本类似物有所改善。此外，本文还简要介绍了Pictet-Spengler工艺，包括产物产率、反应条件、合成产物的光物理性质以及在各个领域的潜在应用。

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来源期刊

Current organic synthesis 化学-有机化学

CiteScore

3.40

自引率

5.60%

发文量

审稿时长

6-12 weeks

期刊介绍： Current Organic Synthesis publishes in-depth reviews, original research articles and letter/short communications on all areas of synthetic organic chemistry i.e. asymmetric synthesis, organometallic chemistry, novel synthetic approaches to complex organic molecules, carbohydrates, polymers, protein chemistry, DNA chemistry, supramolecular chemistry, molecular recognition and new synthetic methods in organic chemistry. The frontier reviews provide the current state of knowledge in these fields and are written by experts who are internationally known for their eminent research contributions. The journal is essential reading to all synthetic organic chemists. Current Organic Synthesis should prove to be of great interest to synthetic chemists in academia and industry who wish to keep abreast with recent developments in key fields of organic synthesis.