Unraveling the access to the regioselective synthesis of highly functionalized pyranopyrazoles using an ionic liquid catalyst

Katariya, Ashishkumar P.; Shirsath, Prakash D; Narode, Hanuman; Gaikwad, Pravinkumar B; Kadam, Gajanan G; Katariya, Maya V.; Deshmukh, Satish U.

doi:10.1007/s11030-022-10572-9

Cited by 4 publications

(1 citation statement)

References 37 publications

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“…[169] Compound 2 exhibited promising anti-bacterial activities and cytotoxic activities (Scheme 12). [170] Some of these catalysts and solvent such as potassium dihydrogen phosphate (KH 2 PO 4 ), [171] ZnO-NiO-Fe 3 O 4 , [172] sulfonated carboxymethylcellulose (CMC-SO 3 H), [173] ionic liquid [(EMIM)Ac], [174,175] glycerol, [176] phenylazophenylenediamine-based La-complex [177] have also been used for the formations of pyranopyrazoles.…”

Section: Synthesis Of Pyranopyrazoles Via Ethyl Acetoacetate Derivativesmentioning

confidence: 99%

Recent Synthesis of Mono‐ & Bis‐Pyranopyrazole Derivatives

Farooq,

Ngaini

2024

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Recent Synthesis of Mono‐ & Bis‐Pyranopyrazole Derivatives. Pyranopyrazole is an important structural unit in heterocyclic chemistry and is useful in pharmaceutical and agrochemical industries. The pyranopyrazole‐based compounds are known in the agricultural industry as herbicides, fungicides, and insecticide agents and in medicinal fields as antimicrobial, anticancer, and antiHIV agents. Despite its wide range of applications, the synthesis of pyranopyrazole has several limitations such as the cost of reagents, potential environmental risks, harsh reaction conditions, longer reaction times, laborious workup procedures, and unsatisfactory yields. However, many studies have been recently reported on the synthesis of pyranopyrazoles using mild, green, and environmentally friendly methods that also give higher yields. Different catalysts and conditions have been reported for the synthesis of pyranopyrazole using four, three, and two components. Among these, four‐component synthesis is commonly reported by using benzaldehyde, hydrazine derivatives, ethyl acetoacetate and malononitrile due to the commercial availability and stability of the reagents. This review summarized the recent synthesis of pyranopyrazole i. e., mono‐ and bis‐pyranopyrazole derivatives via four‐, three‐ and two‐component‐based reactions. Mono‐ and bis‐pyranopyrazole derivatives varied due to the number of pyranopyrazole units that contributed to play an important role in increasing the binding interaction and biological activities beneficial for pharmaceutical industries.

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Section: Synthesis Of Pyranopyrazoles Via Ethyl Acetoacetate Derivativesmentioning

confidence: 99%

Recent Synthesis of Mono‐ & Bis‐Pyranopyrazole Derivatives

Farooq,

Ngaini

2024

ChemistrySelect

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An Expedient Approach for the Regioselective Synthesis of Fully Functionalized and Highly Substituted N‐Methyl‐1,4‐Dihydropyridines Using an Ionic Liquid Catalyst

Katariya,

Kanagare,

Tagad

et al. 2024

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A facile and highly efficient protocol has been developed for the synthesis of extensively functionalized, fully substituted N‐methyl‐1,4‐dihydropyridines. This approach is a one‐pot pseudo‐three‐constituent cyclo‐condensation of aromatic aldehydes with (E)‐N‐methyl‐1‐(methylthio)‐2‐nitroethenamine (NMSM). This reaction presumably entails the Knoevenagel reaction followed by Michael addition and regioselective N‐cyclization with removing methanethiol and producing two C─C bonds and one C─N bond. The key advantages of this strategy include an optimized reaction time, achieving moderate to excellent yields, a straightforward experimental procedure, and the use of the ionic liquid 1‐ethyl‐3‐methylimidazolium acetate [(EMIM)Ac] as the catalyst. The resulting derivatives were well characterized by IR, 1H NMR, 13C NMR, and HRMS.

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