Synthesis of Novel Pyrazolyl and Isoxazolyl 3-(Furan-2-yl)-5-Methyl-1-(4-Nitrophenyl)-1H-Pyrazol-4-yl Derivatives via Regioselectivity of the 1,3-Dipolar Cycloaddition
- 21 May 2023
- journal article
- research article
- Published by Taylor & Francis Ltd in Polycyclic Aromatic Compounds
Abstract
The reaction of 1-(3-(furan-2-yl)-5-methyl-1-(4-nitrophenyl)-1H-pyrazol-4-yl)ethan-1-one 1 with dimethylformamide dimethyl acetal (DMF-DMA) afforded 3-(dimethylamino)-1-(3-(furan-2-yl)-5-methyl-1-(4-nitrophenyl)-1H-pyrazol-4-yl)prop-2-en-1-one 2. Then the treatment of enaminone 2 with the appropriate hydrazonoyl halides 3a-f in chloroform in the presence of triethylamine at reflux gave novel bipyrazolyl methanone derivatives 4a-f. The novel bipyrazole derivatives 4a-c and 4d-f reacted with hydrazine hydrate in ethanol at reflux to give the corresponding pyrazolopyridazinones 9a-c and pyrazolopyridazines 10d-f, respectively. Stirring of hydroximoyl chlorides 11a,b with enaminone 2 in chloroform in the presence of triethylamine at room temperature afforded isoxazole derivatives 12a,b. The reaction of isoxazoles 12a,b with hydrazine hydrate in refluxing ethanol gave the corresponding isoxazolopyridazines 14a,b.Keywords
This publication has 34 references indexed in Scilit:
- Synthesis and biological evaluation of some pyrazolylpyrazolines as anti-inflammatory–antimicrobial agentsEuropean Journal of Medicinal Chemistry, 2010
- Synthesis, anticonvulsant activity and 3D-QSAR study of some prop-2-eneamido and 1-acetyl-pyrazolin derivatives of aminobenzothiazoleEuropean Journal of Medicinal Chemistry, 2010
- Synthesis and antitumor activity of novel α‐aminophosphonates from diterpenic dehydroabietylamineHeteroatom Chemistry, 2008
- Antitumor effects of curcumin and structurally β-diketone modified analogs on multidrug resistant cancer cellsBioorganic & Medicinal Chemistry Letters, 2008
- Anticonvulsant evaluation and mechanism of action of benzylamino enaminonesBioorganic & Medicinal Chemistry, 2006
- Formation of Dihydropyridone- and Pyridone-Based Peptide Analogs through Aza-Annulation of β-Enamino Ester and Amide Substrates with α-Amido Acrylate DerivativesThe Journal of Organic Chemistry, 1997
- Synthesis and Anticonvulsant Activity of Enaminones. 3. Investigations on 4'-, 3'-, and 2'-Substituted and Polysubstituted Anilino Compounds, Sodium Channel Binding Studies, and Toxicity Evaluations1,2Journal of Medicinal Chemistry, 1995
- SYNTHESIS AND REACTIONS OF C-(2-THENOYL)-N-ARYLFORMHYDRAZIDOYL BROMIDESOrganic Preparations and Procedures International, 1988
- Synthesis of heterocycles. Part II. New routes to acetylthiadiazolines and alkylazothiazolesJournal of Heterocyclic Chemistry, 1980
- Reaction of Dimethylphenacylsulfonium Bromide with N-Nitrosoacetarylamides and Reactions of the Products with NucleophilesBulletin of the Chemical Society of Japan, 1976