Zn(Proline) 2-catalyzed Knoevenagel condensation under solventfree/aqueous conditions and biological evaluation of products

Medicinal Chemistry Research

Volumn 20, Issue 9, 2011, Pages 1438-1444

  Siddiqui, Zeba N ^a   Musthafa, T N Mohammed ^a   Praveen, Shagufta ^a   Farooq, Farheen ^a  

^a ALIGARH MUSLIM UNIVERSITY   (India)

Author keywords

5 Chloro 3 methyl 1 phenylpyrazole 4 carboxaldehyde; Antibacterial activity; Antifungal activity; Knoevenagel condensation; Microwave irradiation; Zn(Proline)2

Indexed keywords

2 (5 CHLORO 3 METHYL 1 PHENYLPYRAZOL 4 YL)METHYLENE 1, 3 INDANEDIONE; 2 (5 CHLORO 3 METHYL 1 PHENYLPYRAZOL 4 YL)METHYLENE 1,4 BENZOTHIAZINE 3 ONE; 4 (5 CHLORO 3 METHYL 1 PHENYLPYRAZOL 4 YL)METHYLENE 3 METHYL 1 PHENYLPYRAZOL 5 ONE; 5 (5 CHLORO 3 METHYL 1 PHENYLPYRAZOL 4 YL)METHYLENE 1,3 DIMETHYL 2,4,6 PYRIMIDINETRIONE; 5 (5 CHLORO 3 METHYL 1 PHENYLPYRAZOL 4 YL)METHYLENE 2 MERCAPTO 4,6 PYRIMIDINEDIONE; 5 (5 CHLORO 3 METHYL 1 PHENYLPYRAZOL 4 YL)METHYLENE 2, 2 DIMETHYL 1,3 DIOXANE 4,6 DIONE; 5 (5 CHLORO 3 METHYL 1 PHENYLPYRAZOL 4 YL)METHYLENE 2,4,6 PYRIMIDINETRIONE; 5 CHLORO 3 METHYL 1 PHENYLPYRAZOLE 4 CARBOXALDEHYDE; ANTIBIOTIC AGENT; ANTIFUNGAL AGENT; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; AQUEOUS SOLUTION; ASPERGILLUS FUMIGATUS; ASPERGILLUS NIGER; BACILLUS SUBTILIS; CANDIDA ALBICANS; CATALYSIS; CATALYST; CONFERENCE PAPER; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; KNOEVENAGEL CONDENSATION; NONHUMAN; SALMONELLA TYPHIMURIUM; STAPHYLOCOCCUS AUREUS;

EID: 84856231904     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-010-9376-4     Document Type: Conference Paper

References (32)

1. Bauer AW, Kirby WMM, Sherris JC, Turch M (1966) Antibiotic susceptibility testing by a standardized single disk method. Am J Clin Pathol 45:493-496
2. Bigi F, Chesini L, Maggi R, Sartori G (1999) Montmorillonite KSF as an inorganic, water stable, and reusable catalyst for the Knoevenagel synthesis of coumarin-3-carboxylic acids. J Org Chem 64:1033-1035 (Pubitemid 29098037)
3. Caddick S (1995) Microwave assisted organic reactions. Tetrahedron 51(38):10403-10432
4. Darbre T, Machuqueiro M (2003) Zn-Proline catalyzed direct Aldol reaction in aqueous media. Chem Commun 9:1090-1091 (Pubitemid 36570662)
5. Fang X, Yanping L, Chenjiang L, Li Z (2005) Synthesis of 5-(substituted pyrazolyl-4-methylidyne) (thio) barbituric acid. Huaxue Tongbao 68(12):944-946
6. Galema SA (1997) Microwave chemistry. Chem Soc Rev 26:233-238 (Pubitemid 127097205)
7. Kanizsai I, Gyonfalvi S, Szakonyi Z, Sillanpaa R, Fulop F (2007) Synthesis of bi-and tricyclic b-lactam libraries in aqueous medium. Green Chem 9:357-360
8. Kappe CO, Dallinger D (2009) Controlled microwave heating in modern organic synthesis: Highlights from the 2004-2008 literature. Mol Divers 13:71-193
9. Kofoed J, Machuqueiro M, Reymond JL, Darbre T (2004) Zinγ-proline catalyzed pathway for the formation of sugars. Chem Commun 13:1540-1541 (Pubitemid 38969091)
10. Kofoed J, Reymond JL, Darbre T (2005) Prebiotic carbohydrate synthesis: Zinγ-proline catalyzes direct aqueous Aldol reactions of α-hydroxy aldehydes and ketones. Org Biomol Chem 3:1850-1855 (Pubitemid 40751355)
11. Kofoed J, Darbre T, Reymond JL (2006) Dual mechanism of zincproline catalyzed Aldol reactions in water. Chem Commun 14: 1482-1484
12. Latif FMA, Barsi MA, Maghraby AS, Badr MZA, Dopp D (1995) Preparation of new azole and pyrimidine derivatives. J Indian Chem Soc 72:641-643
13. Li CJ (2005) Organic reactions in aqueous media with a focus on carbon-carbon bond formations: A decade update. Chem Rev 105:3095-3165
14. Lu Y, Ren Z, Cao W, Tong W, Gao M (2004) Solvent-free synthesis of ethyl α-cyanocinnamate in the presence of CaO. Synth Commun 34(11):2047-2051 (Pubitemid 38780515)
15. Meuly WC, Othmer K (1979) Encyclopedia of chemical technology, vol 7. Wiley, New York, p 196
16. Pawar RA, Patil AA (1994) Studies on Vilsmeier-Hack reaction: A versatile new synthesis of 5-chloro-3-methylpyrazole-4-carboxaldehyde, 5-chloro-3-methyl-1-phenylpyrazole-4-carboxaldehyde and related fused heterocyclic compounds and heterocyclic Schiff bases. Indian J Chem 33B:156-158
17. Peng Y, Song G (2003) Microwave-enhanced Knoevenagel reaction catalyzed by calcium oxide. Indian J Chem 42B:924-926
18. Ren YM, Cai C (2007) Knoevenagel condensation of aromatic aldehydes with active methylene compounds using a catalytic amount of iodine andK2CO3 at roomtemperature. Synth Commun 37:2209-2213 (Pubitemid 47037145)
19. Ruben FL, Kofoed J, Machuqueiro M, Darbre T (2005) A selective direct aldol reaction in aqueous media catalyzed by zinγ-proline. Eur J Org Chem 2005:5268-5276
20. Sebti S, Smahi A, Solhy A (2002) Natural phosphate doped with potassium fluoride and modified with sodium nitrate: Efficient catalyst for the Knoevenagel condensation. Tetrahedron Lett 43: 1813-1815 (Pubitemid 34175177)
21. Siddiqui ZN, Asad M (2009) Novel pyrazolopyrones from enol lactones. Indian J Chem 48B:1609-1613
22. Simpson J, Rathbone DL, Billington DC (1999) New solid phase Knoevenagel catalyst. Tetrahedron Lett 40:7031-7033 (Pubitemid 29429586)
23. 2Zn catalysed synthesis of 1,5-benzodiazepine derivatives under solvent-free condition. Synth Commun 34(21): 3833-3846 (Pubitemid 39458619)
24. Sivamurugan V, Vinu A, Palanichamy M, Murugesan V (2006) Rapid and cleaner synthesis of 1,4-dihydropyridine in aqueous medium. Heteroatom Chem 17(4):267-271 (Pubitemid 43799069)
25. Tahmassebi D, Wilson LJA, Kieser JM (2009) Knoevenagel condensation of aldehydes with Meldrum's acid in ionic liquids. Synth Commun 39:2605-2613
26. Tanaka K, Toda F (2000) Solvent-free organic synthesis. Chem Rev 100:1025-1074
27. Tietze LF, Beifuss U (1991) In: Trost BM, Fleming I (eds) Comprehensive organic synthesis, vol 2. Pergamon, Oxford, pp 341-394
28. Varma RS (1999) Solvent-free organic synthesis using supported reagents and microwave irradiation. Green Chem 43-55
29. Vijender M, Kishore P, Satyanarayana B (2008) Zirconium tetrachloride-SiO2 catalyzed Knoevenagel condensation: A simple and efficient protocol for the synthesis of substituted electrophilic alkenes. Arkivoc 13:122-128
30. Wada S, Suzuki H (2003) Calcite and flourite as catalyst for the Knovenagel condensation of malononitrile and methyl cyanoacetate under solvent-free conditions. Tetrahedron Lett 44:399-401 (Pubitemid 35449591)
31. Xing C, Zhu S (2004) Unexpected formation of tetrasubstituted 2,3-dihydro furans from the reactions of b-keto polyfluoroalkanes sulfones with aldehydes. J Org Chem 69:6486-6488 (Pubitemid 39296261)
32. Zhang AQ, Zhang N, Hong S, Zhang M (2009) Leucoemeraldinebase-catalyzed Knoevenagel condensation. Synth Commun 39: 3024-3030