Mg-al hydrotalcite as a first heterogeneous basic catalyst for the synthesis of 4H-pyrano[2,3-c]pyrazoles through a four-component reaction

Synthetic Communications

Volumn 41, Issue 9, 2011, Pages 1320-1325

  Kshirsagar, Siddheshwar W ^a   Patil, Nitin R ^a   Samant, Shriniwas D ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Heterogeneous catalyst; hydrotalcite; multicomponent reactions

Indexed keywords

ACETIC ACID DERIVATIVE; ACETOACETIC ACID ETHYL ESTER; ALCOHOL; ALDEHYDE; HYDRAZINE; HYDROTALCITE; MALONONITRILE; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BINDING; CHEMICAL REACTION; ENVIRONMENTAL TEMPERATURE; MULTICOMPONENT REACTION; ONE POT SYNTHESIS; ROOM TEMPERATURE; STEREOCHEMISTRY;

EID: 79953658748     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.481753     Document Type: Article

References (24)

1. (a) Ugi, I.; Dombling, A.; Werner, B. Since 1995, the new chemistry of multicomponent reactions and their libraries, including their heterocyclic chemistry. J. Heterocycl. Chem. 2000, 37, 647;
2. (b) Bienayme, H.; Hulme, C.; Oddon, G.; Schmitt, P. Maximizing synthetic efficiency: Multicomponent transformations lead the way. Chem. Eur. J. 2000, 6, 3321.
3. (a) Orru, R. V. A.; Greef, M. Recent advances in solution-phase multicomponent methodology for the synthesis of heterocyclic compounds. Synthesis 2003, 1471;
4. (b) Domling, A. Recent developments in isocyanide-based multicomponent reactions in applied chemistry. Chem. Rev. 2006, 106, 17;
5. (c) Zhu, J.; Bienayme, H. Multicomponent Reactions; Wiley-VCH: Weinheim, 2005.
6. El-Tamany, E. S.; El-Shahed, F. A.; Mohamed, B. H. Synthesis and biological activity of some pyrazole derivatives. J. Serb. Chem. Soc. 1999, 64, 9.
7. Zaki, M. E. A.; Soliman, H. A.; Hiekal, O. A.; Rashad, A. E. Pyrazolopyranopyrimidines as a class of anti-inflammatory agents. Z. Naturforsch C 2006, 61, 1.
8. Abdelrazek, F. M.; Metz, P.; Kataeva, O.; Jaeger, A.; El-Mahrouky, S. F. Synthesis and molluscicidal activity of new chromene and pyrano[2,3-c]pyrazole derivatives. Arch. Pharm. 2007, 340, 543.
9. Foloppe, N.; Fisher, L. M.; Howes, R.; Potter, A.; Robertson, A. G. S.; Surgenor, A. E. Identification of chemically diverse Chk1 inhibitors by receptor-based virtual screening. Bioorg. Med. Chem. 2006, 14, 4792.
10. (a) Otto, H. H. Darstellung einiger 4H-Pyrano[2.3-c]pyrazolderivate. Arch. Pharm. 1974, 307, 444;
11. (b) Otto, H. H.; Schmelz, H. Heterocyclen durch Michael-Reaktionen, 5: Mitt. Nucleophile Additionen an 4-Aryliden-pyrazolone. Arch. Pharm. 1979, 312, 478.
12. Sharanin, Y. A.; Sharanina, L. G.; Puzanova, V. V. Nitrile cyclization reactions, VII: Synthesis of 6-amino-4-aryl-3-methyl-5-cyano-1H,4H-pyrazolo[3,4- b]pyrans. Zh. Org. Khim. 1983, 19, 2609.
13. Vasuki, G.; Kumaravel, K. Rapid four-component reactions in water: Synthesis of pyranopyrazoles. Tetrahedron Lett. 2008, 49, 5636.
14. Dyachenko, V. D.; Rusanov, E. B. Novel approaches to synthesis of 4-alkyl-6-amino- 5-cyano-3-methyl(propyl, phenyl)-2H,4H-pyrano[2,3-c]pyrazoles. Chem. Heterocycl. Compd. 2004, 40, 231.
15. Jin, T. S.; Zhao, R. Q.; Li, T. S. An one-pot, three-component process for the synthesis of 6-amino-4-aryl-5-cyano-3-methyl-1-phenyl-1,4- dihydropyrano[2,3-c]pyrazoles in aqueous media. Arkivoc 2006, 176.
16. Jin, T. S.; Wang, A. Q.; Cheng, Z. L.; Zhang, J. S.; Li, T. S. A clean and simple synthesis of 6-amino-4-aryl-5-cyano-3-methyl-1-phenyl-1,4- dihydropyrano[2,3-c]pyrazole in water. Synth. Commun. 2005, 35, 137.
17. Ren, Z.; Cao,W.; Tong,W.; Jin, Z. Solvent-Free, One-pot synthesis of pyrano[2,3-c]pyrazole derivatives in the presence of KF 2H2O by grinding. Synth. Commun. 2005, 35, 2509.
18. Shestopalov, A. M.; Emeliyanova, Y. M.; Shestopalov, A. A.; Rodinovskaya, L. A.; Niazimbetova, Z. I.; Evans, D. H. One-step synthesis of substituted 6-amino-5-cyanospiro- 4-(piperidine-40)- 2H,4H-dihydropyrazolo[3,4-b]pyrans. Org. Lett. 2002, 4, 423.
19. Seshu Babu, N.; Pasha, N.; Venkateswara Rao, K. T.; Sai Prasad, P. S.; Lingaiah, N. A heterogeneous strong basic Mg=La mixed oxide catalyst for efficient synthesis of polyfunctionalized pyrans. Tetrahedron Lett. 2008, 49, 2730.
20. Peng, Y.; Song, G.; Dou, R. Surface cleaning under combined microwave and ultrasound irradiation: Flash synthesis of 4H-pyrano[2,3-c]pyrazoles in aqueous media. Green Chem. 2006, 8, 573.
21. (a) Kshirsagar, S. W.; Patil, N. R.; Samant, S. D. Mg-Al hydrotalcites as the first heterogeneous basic catalysts for the Kornblum oxidation of benzyl halides to benzaldehydes using DMSO. Tetrahedron Lett. 2008, 49, 1160;
22. (b) Surpur, M. P.; Kshirsagar, S. W.; Samant, S. D. Exploitation of the catalytic efficacy of Mg=Al hydrotalcite for the rapid synthesis of 2-aminochromene derivatives via a multicomponent strategy in the presence of microwaves. Tetrahedron Lett. 2009, 50, 719.
23. Cavani, F.; Trifiro, F.; Voccari, A. Hydrotalcite-type anionic clays: Preparation, properties, and applications. Catal. Today 1991, 11, 173.
24. Croma, A.; Fornes, V.; Martin-Aranda, R. M.; Rey, F. Determination of base properties of hydrotalcites: Condensation of benzaldehyde with ethyl acetoacetate. J. Catal. 1992, 134, 58.