A convenient synthesis of functionalized pyrazolones bearing a highly twisted 1,3-butadiene moiety with skew geometry

References

• Bianchini, R.; Bonanni, M.; Corsi, M.; Infantino, A. S. Viable and Straightforward Approach to the Preparation of Water Soluble Pyrazol-5-One Derivatives through Glycoconjugation. Tetrahedron 2012, 68, 8636–8644. DOI: 10.1016/j.tet.2012.07.074.
   Web of Science ®Google Scholar
• Gunasekaran, P.; Perumal, S.; Yogeeswari, P.; Sriram, D. A Facile Four-Component Sequential Protocol in the Expedient Synthesis of Novel 2-Aryl-5-Methyl-2,3-Dihydro-1H-3-Pyrazolones in Water and Their Antitubercular Evaluation. Eur. J. Med. Chem. 2011, 46, 4530–4536. DOI: 10.1016/j.ejmech.2011.07.029.
   PubMed Web of Science ®Google Scholar
• Souza, F. R.; Souza, V. T.; Ratzlaff, V.; Borges, L. P.; Oliveira, M. R.; Bonacorso, H. G.; Zanatta, N.; Martins, M. A. P.; Mello, C. F. Hypothermic and Antipyretic Effects of 3-Methyl- and 3-Phenyl-5-Hydroxy-5-Trichloromethyl-4,5-Dihydro-1H-Pyrazole-1-Carboxyamides in Mice. Eur. J. Pharmacol. 2002, 451, 141–147. DOI: 10.1016/S0014-2999(02)02225-2.
   PubMed Web of Science ®Google Scholar
• Kandhasamy, S.; Ramanathan, G.; Muthukumar, T.; Thyagarajan, S.; Umamaheshwari, N.; Santhanakrishnan, V. P.; Sivagnanam, U. T.; Perumal, P. T. Nanofibrous Matrixes with Biologically Active Hydroxybenzophenazine Pyrazolone Compound for Cancer Theranostics. Mater. Sci. Eng. C Mater. Biol. Appl. 2017, 74, 70–85. DOI: 10.1016/j.msec.2017.01.001.
   PubMed Web of Science ®Google Scholar
• Moneer, A. A.; Khaled, O. M.; El-Nassan, H. B. Synthesis of Novel Substituted Thiourea and Benzimidazole Derivatives Containing a Pyrazolone Ring as anti‐Inflammatory Agents. Chem. Biol. Drug Des. 2016, 87, 784. DOI: 10.1111/cbdd.12712.
   PubMed Web of Science ®Google Scholar
• Metwally, M. A.; Bondock, S. A.; El-Desouky, S. I.; Abdou, M. M. Pyrazol-5-Ones: Tautomerism, Synthesis and Reactions. Int. J. Modern Org. Chem. 2012, 1, 19–54.
   Google Scholar
• Metwally, M. A.; Khalifa, M. E.; Amer, F. A. New Azodisperse Dyes with 4-Hydroxymethyl-2-Pyrazolin-5-One Ring for Dyeing Polyester Fabrics, Part 5. Dyes Pigments 2008, 76, 379. DOI: 10.1016/j.dyepig.2006.08.048.
   Web of Science ®Google Scholar
• Schmidt, A.; Dreger, A. Recent Advances in the Chemistry of Pyrazoles. Properties, Biological Activities, and Syntheses. Coc. 2011, 15, 1423–1463. DOI: 10.2174/138527211795378263.
   Google Scholar
• Fustero, S.; Román, R.; Sanz-Cervera, J. F.; Simón-Fuentes, A.; Bueno, J.;.; Villanova, S. Synthesis of New Fluorinated Tebufenpyrad Analogs with Acaricidal Activity through Regioselective Pyrazole Formation. J. Org. Chem. 2008, 73, 8545. DOI: 10.1021/jo801729p.
   PubMed Web of Science ®Google Scholar
• Eicher, T.; Hauptmann, S.; Speicher, A. The Chemistry of Heterocycles. Structure, Reactions, Synthesis, and Applications. Wiley-VCH: Weinheim, 2012; p. 243.
   Google Scholar
• Sadjadi, S.; Heravi, M. M. Recent Application of Isocyanides in Synthesis of Heterocycles. Tetrahedron 2011, 67, 2707–2752. DOI: 10.1016/j.tet.2011.01.086.
   Web of Science ®Google Scholar
• Jiang, B.; Rajale, T.; Wever, W.; Tu, S.-J.; Li, G. Multicomponent Reactions for the Synthesis of Heterocycles. Chem Asian J. 2010, 5, 2318. DOI: 10.1002/asia.201000310.
   PubMed Web of Science ®Google Scholar
• Zhu, J. Recent Developments in the Isonitrile‐Based Multicomponent Synthesis of Heterocycles. Eur. J. Org. Chem. 2003, 2003, 1133. DOI: 10.1002/ejoc.200390167.
   Web of Science ®Google Scholar
• Nair, V.; Rajesh, C.; Vinod, A.; Bindu, S.; Sreekanth, A.; Mathen, J.; Balagopal, L. Strategies for Heterocyclic Construction via Novel Multicomponent Reactions Based on Isocyanides and Nucleophilic Carbenes. Acc. Chem. Res. 2003, 36, 899. DOI: 10.1021/ar020258p.
   PubMed Web of Science ®Google Scholar
• Dömling, A. Recent Advances in isocyanide-based multicomponent chemistry. Curr. Opin. Chem. Biol. 2002, 6, 306–313. DOI: 10.1016/S1367-5931(02)00328-9.
   PubMed Web of Science ®Google Scholar
• Yavari, I.; Naeimabadi, M. Synthesis of 3-(Quinolin-2-yl)Indolizines through Iodine-Mediated sp3C–H Functionalization of Azaarenes. Synth. Commun. 2018, 48, 632. DOI: 10.1080/00397911.2017.1362436.
   Web of Science ®Google Scholar
• Yavari, I.; Amirahmadi, A.; Halvagar, M. R. A Synthesis of Functionalized Thiazoles and Pyrimidine-4-(3H)-Thiones from 1,1,3,3-Tetramethylguanidine, Acetylenic Esters, and Aryl Isothiocyanates. Synlett 2017, 28, 2629–2632. DOI: 10.1055/s-0036-1590862.
   Web of Science ®Google Scholar
• Sadegh-Samiei, S.; Yavari, I.; Skoulika, S. Base‐Catalyzed Formation of Isoxazoles from Dialkyl Acetylenedicarboxylates and 2‐Nitroacetophenones. Helv. Chim. Acta. 2015, 46, 36.
   Google Scholar
• Farrugia, L. J. WinGX Suite for Small-Molecule Single-Crystal Crystallography. J. Appl. Crystallogr. 1999, 32, 837–838. DOI: 10.1107/S0021889899006020.
   Web of Science ®Google Scholar
• Allen, F. H.; Johnson, O.; Shields, G. P.; Smith, B. R.; Towler, M. CIF Applications. XV. enCIFer: A Program for Viewing, Editing and Visualizing CIFs. J. Appl. Crystallogr. 2004, 37, 335–338. DOI: 10.1107/S0021889804003528.
   Web of Science ®Google Scholar
• Macrae, C. F.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Shields, G. P.; Taylor, R.; Towler, M.; van de Streek, J. Mercury: visualization and Analysis of Crystal Structures. J. Appl. Crystallogr. 2006, 39, 453–457. DOI: 10.1107/S002188980600731X.
   Web of Science ®Google Scholar
• Burnett, M. N.; Johnson, C. K. ORTEP-III: Oak Ridge Thermal Ellipsoid Plot Program for Crystal Structure Illustrations. Oak Ridge National Laboratory: Tennessee, 1996.
   Google Scholar