Green one pot solvent-free synthesis of pyrano[2,3-c]-pyrazoles and pyrazolo[1,5-a]pyrimidines

Molecules

Volumn 15, Issue 9, 2010, Pages 6619-6629

  Al Matar, Hamad M ^a   Khalil, Khaled D ^b   Adam, Aisha Y ^a   Elnagdi, Mohamed H ^a  

^a KUWAIT UNIVERSITY   (Kuwait)

^b CAIRO UNIVERSITY   (Egypt)

Author keywords

Aminopyrazolinone; Cyanoacetic acetic anhydride; Multi component synthesis; NOE difference experiments; Pyranopyrazole; Pyrazolo 1,5 a pyrimidine

Indexed keywords

PYRAZOLE DERIVATIVE; PYRIMIDINE DERIVATIVE;

ARTICLE; GREEN CHEMISTRY; SYNTHESIS;

GREEN CHEMISTRY TECHNOLOGY; PYRAZOLES; PYRIMIDINES;

EID: 77957302251     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules15096619     Document Type: Article

References (21)

1. Otto, H. H. Synthesis of Some 4H-Pyrano[2.3-c]pyrazoles. Arch. Pharm. 1974, 307, 444-447.
2. Abdou, S.; Fahmy, S. M.; Sadek, K. U.; Elnagdi, M. H. Activated nitriles in heterocyclic synthesis: A novel synthesis of pyrano[2, 3-c]pyrazoles. Heterocycles 1981, 16, 2177-2180.
3. Shestopalov, A. M.; Emel'yanova Y. M.; Shestopalov, A. A.; Rodinovskaya, L. A.; Niazimbetova, Z. I.; Evans, D. H. Cross-condensation of derivatives of cyanoacetic acid and carbonyl compounds. Part 1: Single-stage synthesis of 1′-substituted 6-amino-spiro-4-(piperidine-4′)-2H, 4H-pyrano[2, 3-c]pyrazole-5-carbonitriles. Tetrahedron 2003, 59, 7491-7496.
4. 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.
5. 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, 9-18.
6. Girgis, N. S.; Elgemeie, G. A. M.; Nawar, G. A. M.; Elnagdi, M. H. α, β-Unsaturated nitriles in heterocyclic synthesis: The reaction of β - (2-furanyl) - and β - (2-thienyl) acrylonitrile with active methylene reagents. Liebigs. Ann. Chem. 1983, 1468-1475.
7. Shestopalov, A. M.; Yakubov, A. P.; Tsyganov, D. V.; Emel'yanova, Y. M.; Nesterov, V. N. Synthesis of substituted 6-amino-4-aryl-5-cyano-2H, 4H-pyrano[2, 3-c]pyrazoles. Crystal and molecular structure of 6-amino-5-cyano-3-methyl-4- (2′, 4′, 6′-triethylphenyl)-2H, 4H-pyrano[2, 3-c]pyrazole. Chem. Heterocycl. Compds. 2002, 38, 1180-1189.
8. Redkin, R. G.; Shemchuk, L. A.; Chernykh, V. P.; Shishkin, O. V.; Shishkina, S. V. Synthesis and molecular structure of spirocyclic 2-oxindole derivatives of 2-amino-4H-pyran condensed with the pyrazolic nucleus. Tetrahedron 2007, 63, 11444-11450.
9. Rodinovskaya, L.; Shestopalov, A.; Gromova, A.; Shestopalov, A. Substituted 4-(3-cyanopyridin-2-ylthio) acetoacetates: New convenient reagents for the synthesis of heterocycles. Synthesis 2006, 2357-2370.
10. Rodinovskaya, L. A.; Gromova, A. V.; Shestopalov, A. M.; Nesterov, V. N. Synthesis of 6-amino-4-aryl-5-cyano-3-(3-cyanopyridin-2-ylthiomethyl)-2, 4-dihydropyrano[2, 3-c]pyrazoles and their hydrogenated analogs. Molecular structure of 6-amino-5-cyano-3-(3-cyano-4, 6-dimethylpyridin-2-ylthiomethyl)-4- (2-nitrophenyl)-2, 4-dihydropyrano[2, 3-c]pyrazole. Russ. Chem. Bull. 2003, 52, 2207-2213.
11. Metwally, N. H.; Abdelrazek, F. M.; Sobhy, N. A. About the reaction of α-substituted cinnamonitriles with 3-substituted and 1, 3-disubstituted pyrazolin-5-ones. Afinidad 2005, 62, 616.
12. Abdelrazek, F. M.; Metz, P.; Metwally, N. H.; El-Mahrouky, S. F. Synthesis and molluscicidal activity of new cinnoline and pyrano [2, 3-c]pyrazole derivatives. Arch. Pharm. Chem. Life Sci. 2006, 339, 456-460.
13. Lehmann, F.; Holm, M.; Laufer, S. Three-component combinatorial synthesis of novel dihydropyrano[2, 3-c]pyrazoles. J. Comb. Chem. 2008, 10, 364-367.
14. Al-Matar, H. M.; Khalil, K. D.; Meier, H.; Kolshorn, H.; Elnagdi, M. H. Chitosan as heterogeneous catalyst in Michael additions: The reaction of cinnamonitriles with active methylene moieties and phenols. Arkivoc 2008, xvi, 288-301.
15. Vasuki, G.; Kumaravel, K. Rapid four-component reactions in water: Synthesis of pyranopyrazoles. Tetrahedron Lett. 2008, 49, 5636-5638.
16. Gogoi, S.; Zhao, C. Organocatalyzed enantioselective synthesis of 6-amino-5-cyanodihydropyrano[2, 3-c]pyrazoles. Tetrahedron Lett. 2009, 50, 2252-2255.
17. Litvinov, Y. M.; Shestopalov, A. A.; Rodinovskaya, L. A.; Shestopalov, A. M. New Convenient Four-Component Synthesis of 6-Amino-2, 4-dihydropyrano[2, 3-c]pyrazol-5-carbonitriles and One-Pot Synthesis of 6′-Aminospiro[(3H)- indol-3, 4′-pyrano[2, 3-c]pyrazol]-(1H)-2-on-5′-carbonitriles. J. Comb. Chem. 2009, 11, 914-919.
18. Nagarajan, A. S.; Reddy, B. S. R. Synthesis of substituted pyranopyrazoles under neat conditions via a multicomponent reaction. Synlett 2009, 12, 2002-2004.
19. Khalil, K. D.; Al-Matar, H. M.; Al-Dorri, D. M.; Elnagdi, M. H. Studies with enaminones and enaminonitriles: Synthesis of 3-aroyl- and 3-heteroaroylpyrazolo[1, 5-a]pyrimidines. Tetrahedron 2009, 65, 9421-9427.
20. Anwar, H. W.; Fleita, D. H.; Kolshorn, H.; Meier, H.; Elnagdi, M. H. 2H-3-Pyrazolamines as precursors for the synthesis of polyfunctionally substituted pyrazolo[1, 5-a]pyrimidines. ARKIVOC 2006, xv, 133-141.
21. Abdel Galil, F. M.; Abdel Motaleb, R. M.; Elnagdi, M. H. Nitriles in heterocyclic synthesis: The reaction of acetophenonylidenemalononitrile with some active methylene reagents and acrylonitrile derivatives. Anales de Quimica, Serie C: Quimica Organica y Bioquimica 1988, 84, 19-21.