132813-99-1

Usage

Uses

Used in Pharmaceutical Industry:
6-AMINO-3-METHYL-4-(3-PYRIDINYL)-1,4-DIHYDROPYRANO[2,3-C]PYRAZOLE-5-CARBONITRILE is used as a key intermediate in the synthesis of chromene and pyrano[2,3-c]pyrazole derivatives for their molluscicidal activity. These derivatives have potential applications in the development of drugs to treat parasitic infections, particularly those caused by mollusks.
Used in Chemical Research:
6-AMINO-3-METHYL-4-(3-PYRIDINYL)-1,4-DIHYDROPYRANO[2,3-C]PYRAZOLE-5-CARBONITRILE is also used in chemical research for the exploration of new synthetic pathways and the development of novel compounds with potential applications in various fields, such as pharmaceuticals, materials science, and agrochemicals.

Upstream product

• 500-22-1 3-pyridinecarboxaldehyde 
• 141-97-9 ethyl acetoacetate 
• 109-77-3 malononitrile 
• 7803-57-8 hydrazine hydrate 
• 7424-56-8 2-(3-pyridylmethylene)malononitrile 
• 108-26-9 3-methyl-2-pyrazoline-5-one 

Relevant academic research and scientific papers

Convenient synthesis, characterization, cytotoxicity and toxicity of pyrazole derivatives

3-Methyl-1H-pyrazol-5(4H)-one (1) was used as a template to develop new anticancer compounds and investigate their SAR. The ring modification of compound 1 occurred through its reaction with aromatic aldehydes and various reagents to afford the corresponding 6-oxopyrano[2,3-c]pyrazoles 4a-c and their amino analogues 6-aminopyrano[2,3-c]pyrazoles 6a-c,8; the pyrazolopyrano[2,3-b]pyridines 10a-c and the chromenopyrano[2,3-c]pyrazolones 13,14. The reaction of 1 with thiourea and appropriate aromatic aldehydes afforded the pyrazolo[3,4-d]pyrimidine derivatives 17a-c. On the other hand, the pyrazolo[3,4-d]thiazole derivatives 22a-d were obtained via the reaction of 1 with sulfur and aryl isothiocyanates in the presence of triethylamine. The reaction of 1 with phenylisothiocyanate followed by treatment with the α-halocarbonyl compounds 24a-c afforded the thiazole derivatives 25a-c. The synthesized products were evaluated for their cytotoxicity against cancer and normal cell lines. Most compounds showed significant anticancer activity without affecting the normal fibroblast cells. The toxicity of the most pontent cytotoxic compounds was measured using Brine-Shrimp Lethality Assay.

A green and clean pathway: One pot, multicomponent, and visible light assisted synthesis of pyrano[2,3-: C] pyrazoles under catalyst-free and solvent-free conditions

A mild, eco-efficient and metal-free synthetic protocol for the production of biologically significant scaffold dihydropyrano[2,3-c]pyrazoles via reaction between ethylacetoacetate (1), hydrazine hydrate (2), aromatic aldehydes (3) and malononitrile (4) a

Morpholine triflate promoted one-pot, four-component synthesis of dihydropyrano[2,3-c]pyrazoles

A one-pot, four-component reaction of ethyl acetoacetate, hydrazine hydrate, aldehydes, and malononitrile was discussed using Lewis acid catalyst morpholine triflate (MorT) to afford a series of dihydropyrano[2,3-c]pyrazoles, which were generally catalyze

A catalyst-free green protocol for the synthesis of pyranopyrazoles using room temperature ionic liquid choline chloride-urea

An efficient and rapid four component reaction of aldehydes, malanonitrile, β-ketoesters and hydrazine hydrate (or phenyl hydrazine) in environmentally benign room temperature ionic liquid choline chloride-urea has been developed for the synthesis of substituted 4H-pyrano[2,3-c]pyrazoles.

Multicomponent synthesis of dihydropyrano[2,3-c]pyrazoles catalyzed by lipase from Aspergillus niger

Lipase from Aspergillus niger (ANL) was found to be an extremely effective catalyst for four-component synthesis of dihydropyrano[2,3-c]pyrazoles from a stoichiometric mixture of ethyl acetoacetate, hydrazine hydrate, aldehyde/ketone, and malononitrile in

Eco-friendly synthesis and biological evaluation of substituted pyrano[2,3-c]pyrazoles

An ecofriendly green approach for synthesis of substituted pyrano[2,3-c]pyrazoles has been developed via a multicomponent one pot approach in aqueous ethanol medium under totally non-catalytic conditions. The synthesized compounds were evaluated for their

Rapid four-component reactions in water: synthesis of pyranopyrazoles

An environmentally benign four-component reaction in aqueous medium at room temperature has been developed for the synthesis of 6-amino-5-cyano-3-methyl-4-aryl/heteroaryl-2H,4H-dihydropyrano[2,3-c]pyrazoles.

Heterocycles Synthesis through Reactions of Nucleophiles with Acrylonitriles, Part 9. A Direct One-Pot Synthesis of Pyranopyrazoles

Several pyranopyrazoles were synthesized through a convenient one-pot method in excellent yields.Structure and reaction pathways are also reported and supported by another synthetic route.