Synthesis of functionalized dihydro-2-oxypyrroles and tetrahydropyridines using 2,6-pyridinedicarboxylic acid as an efficient and mild organocatalyst

Khan, Md. Musawwer; Iqbal, Sajid; Saigal,; Yousuf, Raveed

doi:10.1039/c6nj01170e

Cited by 40 publications

(17 citation statements)

References 78 publications

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“…have been used for the construction of THPD ring. Recently, anionic surfactants sodium dioctylsulfosuccinate (SDOSS), Calix[n]arenes, ethylenediammoniumdiformate (EDDF), cyanuric acid, graphene oxide, polyphosphoric acid supported on silica‐coated magnetic nanoparticles and Bi(III) immobilized on triazine dendrimer stabilized magnetic nanoparticles (Fe 3 O 4 @TDSN−Bi(III)) have been utilized to synthesize this six‐membered nitrogen containing compound. Last year, we published a review article, which uncovered various synthetic strategies developed in the past decade for manufacturing THPD compounds …”

Section: Resultsmentioning

confidence: 99%

Efficient and Eco‐Friendly One‐Pot Synthesis of Functionalized Furan‐2‐one, Pyrrol‐2‐one, and Tetrahydropyridine Using Lemon Juice as a Biodegradable Catalyst

Khan

Saigal

et al. 2018

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New and facile one‐pot approach for the syntheses of polysubstituted pyrrol‐2‐one, furan‐2‐one and tetrahydropyridines (THPDs) from easily available starting materials using lemon juice as a green catalyst is presented. The synthesis of diverse furan‐2‐one and pyrrol‐2‐one derivatives were achieved from dialkyl acetylenedicarboxylates, different amines and aldehydes in high yields and short reaction times by employing 0.25 mL of lemon juice at 110 oC under solvent‐free condition. THPDs, on the other hand, were synthesized via the reaction among β‐ketoesters, various aromatic aldehydes, and amines in the presence of 0.25 mL of lemon juice in ethanol at room temperature. The molecular structure of compound pyrrol‐2‐one 7e and THPD 10g were confirmed by the single crystal X‐ray analysis. Application of cheap and green catalyst, environmentally benign reaction condition, good to high yields, applicable to a broad range of substrates and no column chromatographic separation are some salient features of this protocol.

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Section: Resultsmentioning

confidence: 99%

Efficient and Eco‐Friendly One‐Pot Synthesis of Functionalized Furan‐2‐one, Pyrrol‐2‐one, and Tetrahydropyridine Using Lemon Juice as a Biodegradable Catalyst

Khan

Saigal

et al. 2018

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“…Newly synthesized THPs ( 1 ‐ 3 ) were characterized based on IR, NMR ( 1 H, 13 C, and NOESY), and UV experimental and simulated spectral properties, as well as elemental analysis. For simulation of spectral properties and antioxidative mechanisms, the starting geometry of all examined compounds was based on the crystallographic structure of a similar compound obtained from the literature . Firstly, optimizations were performed in gas phase to confirm the crystallographic structure, and so obtained structures were used for IR spectral characterization.…”

Section: Resultsmentioning

confidence: 99%

One‐Pot Synthesis of Tetrahydropyridine Derivatives: Liquid Salt Catalyst vs Glycolic Acid Promoter. Structure and Antiradical Activity of the New Products

et al. 2017

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Diethanolammonium hydrogensulfate (DHS), as a liquid salt, and glycolic acid (GA) were used for the synthesis of highly functionalized tetrahydropyridines (THPs). Due to the simplicity of the reaction procedure, excellent diastereoselectivity, and catalyst regeneration, these green protocols may be considered as an attractive approach for the preparation of THPs. Unlike numerous reported reactions for the synthesis of THPs that last for hours and with heating, GA‐promoted reactions finished mostly within an hour and at room temperature. As improvement to other organocatalysed reactions for the synthesis of THPs with moderate yields, this protocol provided good to excellent yields. Application of these procedures produced three vanillic compounds reported here for the first time. Their structure was elucidated based on experimental and theoretical data (IR, 1H NMR, 13C NMR, NOESY, UV‐Vis, and DFT). Experimental and theoretical antioxidant evaluation of these compounds has been carried out. DFT thermodynamical parameters supported experimental results that newly synthesized THPs deserve considerable attention as potent radical scavengers.

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“…Khan et al . demonstrated the synthesis of functionalized piperidines using a catalytic amount of 2,6‐pyridinedicarboxylic acid (2,6‐PDCA) in methanol at room temperature (Scheme ).…”

Section: Organo‐catalyzed Synthesis Of 126‐triaryl‐4‐arylamino‐pipementioning

confidence: 99%

One‐Pot Pseudo Five Component Synthesis of Biologically Relevant 1,2,6‐Triaryl‐4‐arylamino‐piperidine‐3‐ene‐3‐ carboxylates: A Decade Update

Kaur¹,

Devi²,

Kumari³

et al. 2018

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Piperidines, an important class of N‐heterocycles, are very common in naturally occurring bioactive compounds. Recently, functionalized piperidines, specifically, 1,2,6‐triaryl‐4‐arylamino‐piperidine‐3‐ene‐3‐carboxylates have drawn considerable attention due to its diverse pharmacological efficacies that include anti‐cancer, anti‐microbial, anti‐oxidant, anti‐fungal, anti‐inflammatory and acetylcholinesterase (AChE) inhibitory activities. As a result, during the last decade, a number of methods reported for the synthesis of 1,2,6‐triaryl‐4‐arylamino‐piperidine‐3‐ene‐3‐carboxylates via one‐pot pseudo five‐component reactions of aromatic aldehydes, anilines and β‐keto esters under various reaction conditions. The present review deals with the ‘‘up to date” developments on the synthesis of 1,2,6‐triaryl‐4‐arylamino‐piperidine‐3‐ene‐3‐carboxylates reported so far.

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Synthesis of functionalized dihydro-2-oxypyrroles and tetrahydropyridines using 2,6-pyridinedicarboxylic acid as an efficient and mild organocatalyst

Abstract: Simple and mild one-pot protocols for the synthesis of diversely functionalized dihydro-2-oxypyrroles and tetrahydropyridines using catalytic amounts of 2,6-PDCA.

Cited by 40 publications

References 78 publications

Efficient and Eco‐Friendly One‐Pot Synthesis of Functionalized Furan‐2‐one, Pyrrol‐2‐one, and Tetrahydropyridine Using Lemon Juice as a Biodegradable Catalyst

Efficient and Eco‐Friendly One‐Pot Synthesis of Functionalized Furan‐2‐one, Pyrrol‐2‐one, and Tetrahydropyridine Using Lemon Juice as a Biodegradable Catalyst

One‐Pot Synthesis of Tetrahydropyridine Derivatives: Liquid Salt Catalyst vs Glycolic Acid Promoter. Structure and Antiradical Activity of the New Products

One‐Pot Pseudo Five Component Synthesis of Biologically Relevant 1,2,6‐Triaryl‐4‐arylamino‐piperidine‐3‐ene‐3‐ carboxylates: A Decade Update

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