Reaction between 4-Nitro-1,3-diarylbutan-1-ones and Ammonium Acetate in the Presence of Morpholine and Sulfur: An Efficient Synthesis of 2,4-Diarylpyrroles

Adib, Mehdi; Ayashi, Neda; Heidari, Fatemeh; Mirzaei, Peiman

doi:10.1055/s-0035-1561852

Cited by 26 publications

(11 citation statements)

References 8 publications

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“…In continuation of our endeavours towards the synthesis of biologically active organic compounds from readily accessible precursors, in this work we sought to explore an efficient four‐component synthesis of functionalized thiophenes from 1,3‐dicarbonyl compounds, aldehydes, activated methylene halides and elemental sulfur (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

A Consecutive Four‐Component Synthesis of Polysubstituted Thiophenes in Aqueous Medium

et al. 2018

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An efficient and straightforward four‐component synthesis of mono‐, bi‐ and tricyclic thiophenes from C–C + C + C + S atom fragments from 1,3‐dicarbonyl compounds, aldehydes, activated methylene halides and elemental sulfur in aqueous medium is described. Arylidene‐1,3‐dicarbonyls, N‐phenacylpyridinium bromides/N‐(p‐nitrobenzyl)pyridinium chloride, pyridinium ylides and 2,3‐dihydrofurans are believed to be the key intermediates of these consecutive transformations. This synthetic strategy provides a potential route to the construction of a library of highly substituted thiophenes with a large substrate scope in good‐to‐excellent yields.

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Section: Resultsmentioning

confidence: 99%

A Consecutive Four‐Component Synthesis of Polysubstituted Thiophenes in Aqueous Medium

et al. 2018

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“…Added to a solution of 1 mmol of substituted phenacyl bromide (78) were 1 mmol substituted amino unsaturated ketone (79) and 10 mol% of BF 3 OEt 3 in dichloromethane and the mixture was irradiated with MWs for 10-16 min at 130°C (250 W). Adib et al [27] showed the reaction of 4-nitro-1, 3-diarylbutan-1-ones (81) and ammonium acetate (82) in the presence of morpholine and sulphur provides the corresponding 2, 4-diarylpyrroles (83) in excellent yields. Morpholine is used to create all volatile environment and also due to its slow decomposition at high temperatures and pressures.…”

Section: Resultsmentioning

confidence: 99%

“…Wang et al [12] synthesized 2, 4-and 2, 3, 4-substituted pyrroles (27) in two or three steps from commercially available ketones (26) and allyl hydroxylamine. An iridium-catalyzed isomerization reaction was developed to convert o-allyl oximes to o-vinyl oximes, which undergo a facile [3,3] rearrangement to form 1, 4-imino aldehyde Paal-Knorr intermediates that cyclized to afford the corresponding pyrroles.…”

Section: Methodsmentioning

confidence: 99%

Simple and Multi-Component Synthesis of Pyrrole Heterocycles

Dar¹,

Mir²,

Zaman³

et al. 2017

Synth Catal

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Pyrroles is the special class of heterocyclic compounds with a broad spectrum of biological activities such as anti-inflammatory, antiproliferative, antihistaminic, anti-HIV, antifungal, antihelmintic and antiviral agents. Pyrrole is a five membered ring structure, with formula C 4 H 4 NH. The heterocyclic pyrroles are the ideal building blocks for different biologically efficient molecules including porphyrins and bile pigments. Therefore researchers are synthesizing these heterocycles through multi-stepped or single stepped pathways as target structures for biological studies. In this review, different synthetic protocols/methodologies are shown in which different entry molecules are converted into pyrrole derivatives, which are important from medicinal and pharmaceutical points of view.

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“…In 2016 Adib et al . reported a method of synthesis of 2,4‐diphenylpyrrole ( 6 ) that involved the reaction of 4‐nitro‐1,3‐diarylbutan‐1‐one with ammonium acetate in the presence of morpholine and elemental sulfur.…”

Section: Figurementioning

confidence: 99%

Accessing Symmetrical Tetraphenyl‐pyrrole‐2‐yl Squaraines Through an Improved Synthesis of 2,4‐Diphenylpyrrole

et al. 2020

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Synthesis of tetraphenyl‐pyrrole‐2‐yl squaraines is introduced for the first time. An improved, reproducible and straightforward method for the preparation of 2,4‐diphenylpyrrole‐a key structural synthon for the preparation of the squaraines in question‐is reported. Both, squaraine dyes and all intermediates were fully characterized using spectroscopic methods, viz. 1H NMR, 13C NMR, 2D NMR (COSY, HSQC, HMBC), FT‐ATR‐IR, ESI‐HRMS. The structures of tetraphenyl‐pyrrol‐2‐yl squaraines were unambiguously confirmed by single X‐ray analysis. The squaraines studied exhibit an intense absorption bands spanning from ca. 600 to 700 nm, entering to the spectral region, which is highly sought after for biomedical applications and advanced material technologies.

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Reaction between 4-Nitro-1,3-diarylbutan-1-ones and Ammonium Acetate in the Presence of Morpholine and Sulfur: An Efficient Synthesis of 2,4-Diarylpyrroles

Abstract: An efficient synthesis of 2,4-diarylpyrroles is described.Heating a mixture of a 4-nitro-1,3-diarylbutan-1-one and ammonium acetate in the presence of morpholine and sulfur afforded the corresponding 2,4-diarylpyrroles in excellent yields.

Cited by 26 publications

References 8 publications

A Consecutive Four‐Component Synthesis of Polysubstituted Thiophenes in Aqueous Medium

A Consecutive Four‐Component Synthesis of Polysubstituted Thiophenes in Aqueous Medium

Simple and Multi-Component Synthesis of Pyrrole Heterocycles

Accessing Symmetrical Tetraphenyl‐pyrrole‐2‐yl Squaraines Through an Improved Synthesis of 2,4‐Diphenylpyrrole

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