A new synthesis of porphyrins <i>via</i> a putative <i>trans</i>-manganese(<scp>iv</scp>)-dihydroxide intermediate

Mondal, Sruti; Sahu, Kasturi; Patra, Bratati; Jena, Subhrakant; Biswal, Himansu S.; Kar, Sanjib

doi:10.1039/c9dt03573g

Cited by 6 publications

(12 citation statements)

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“…The main problem in porphyrin synthesis is its low yields (6%–20%) although different trials to enhance the yields of porphyrins are reported [24–26]. Recently, Fadda et al [27,28] reported a new methodology, which yields 70%–80% yield.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, biological evaluation, and docking studies of various β‐substituted porphyrin conjugates embedded with N‐containing heterocycles

Masaret

2021

Journal of Heterocyclic Chem

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A new methodology for the synthesis of some new β‐porphyrin heterocyclic compounds containing nitrogen derivatives 10, 12, 13, 15, 17, 19, 21, 22, 25, 27, and 29 was screened for their cytotoxic activities. Both elemental and spectral analyses were used to confirm the structures of new compounds. Compounds 22, 27, and 21 exhibited very strong activity against the HepG2 cell line. Investigation of the binding between porphyrin 22 and the binding site of telomerase was performed by molecular docking.

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Section: Resultsmentioning

confidence: 99%

Synthesis, biological evaluation, and docking studies of various β‐substituted porphyrin conjugates embedded with N‐containing heterocycles

Masaret

2021

Journal of Heterocyclic Chem

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“…Kar and co-workers [ 133 , 134 ] have recently developed a new simple two-step method for the synthesis of symmetrical and unsymmetrical meso -arylporphyrins. The first step is the condensation of pyrrole or dipyrromethane with an aldehyde in aqueous methanol in the presence of HCl (Scheme 5 ).…”

Section: Principal Methodologies Of the Synthesis Of Tetrapyrrole Mac...mentioning

confidence: 99%

Main Strategies for the Synthesis of meso-Arylporphyrins

Койфман

Агеева

2022

Russ J Org Chem

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meso -Arylporphyrins as most accessible tetrapyrrole macroheterocycles have always been the focus of attention from researchers concerned with practically useful properties of these compounds. The first syntheses of meso -arylporphyrins date back to about 90 years ago. Up to now, the yields of these compounds have been improved from 5 to 80%. The present review analyzes different ways and strategies for the synthesis of meso -aryl-substituted porphyrins. The most efficient methods that can be scaled up to an industrial level have been identified.

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“…1 H NMR (400 MHz, chloroform- d ) δ 8.85 (s, 8H), 8.25–8.19 (m, 8H), 7.79–7.72 (m, 12H), −2.78 (s, 2H) (Figure S1). Other analytical data are consistent with those of the previously reported authentic compounds …”

Section: Methodsmentioning

confidence: 99%

“…1 H NMR (400 MHz, chloroform- d ) δ 8.86 (s, 8H), 8.13 (d, J = 8.0 Hz, 8H), 7.29 (d, J = 8.0 Hz, 8H), 4.10 (s, 12H), −2.75 (s, 2H) (Figure S2). Other analytical data are consistent with those of the previously reported authentic compounds …”

Section: Methodsmentioning

confidence: 99%

“…Other analytical data are consistent with those of the previously reported authentic compounds. 37 Synthesis of 5,15-Bis(4-bromophenyl)-10,20-(4methylphenyl)porphyrin, 27. 5-(4-Bromophenyl)dipyrromethane (301 mg) (1 mmol) and 117 μL (1 mmol) of p-tolualdehyde were added to a mixture of 100 mL of MeOH and 50 mL of water (2:1), followed by the addition of 10 mL of HCl.…”

Section: ■ Conclusionmentioning

confidence: 99%

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Large-Scale Green Synthesis of Porphyrins

et al. 2021

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A new methodology for porphyrin synthesis has been developed. This is a simple two-step protocol. The first step involves the condensation of pyrrole and aldehyde in an H2O–MeOH mixture using HCl. The obtained precipitate from the first step was dissolved in reagent-grade dimethylformamide (DMF) and refluxed for 1.5 h, followed by stirring overnight in the air at room temperature. Subsequent purification through column chromatography or crystallization resulted in the formation of pure porphyrins. Advantageously, this methodology does not need any expensive chemicals such as 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ), chloranil, and so forth as an oxidizing agent. This reaction also does not require a large volume of dry chlorinated solvents. Contrary to the reported methodologies, which are mostly ineffective in the gram-scale production of porphyrins, the present method perfectly caters to the need for gram-scale production of porphyrins. In essence, the current methodology does not represent the synthesis having the highest yield in the literature. However, it represents the easiest and cheapest synthesis of porphyrin on a large scale to obtain a reproducible yield of 10–40% with high purity. In a few of the examples, even column chromatography is not necessary. A simple crystallization technique will be sufficient to generate the desired porphyrins in good yields.

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A new synthesis of porphyrins via a putative trans-manganese(iv)-dihydroxide intermediate

Abstract: An efficient, milder (occurs at RT), scalable, and environmentally benign methodology for the facile synthesis of porphyrin derivatives without using quinone based oxidants has been developed.

Cited by 6 publications

References 76 publications

Synthesis, biological evaluation, and docking studies of various β‐substituted porphyrin conjugates embedded with N‐containing heterocycles

Synthesis, biological evaluation, and docking studies of various β‐substituted porphyrin conjugates embedded with N‐containing heterocycles

Main Strategies for the Synthesis of meso-Arylporphyrins

Large-Scale Green Synthesis of Porphyrins

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