A practical catalyst-free synthesis of 6-amino-4 alkyl/aryl-3-methyl-2,4- dihydropyrano[2,3-c]pyrazole-carbonitrile in aqueous medium

Journal of Chemistry

Volumn , Issue , 2013, Pages

  Bihani, Manisha ^a   Bora, Pranjal P ^a   Bez, Ghanashyam ^a  

^a NORTH EASTERN HILL UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84869014039     PISSN: 20909063     EISSN: 20909071     Source Type: Journal    
DOI: 10.1155/2013/920719     Document Type: Article

References (47)

1. Touré B. B., Hall D. G., Natural product synthesis using multicomponent reaction strategies. Chemical Reviews 2009 109 9 4439 4486 2-s2.0-70349156384 10.1021/cr800296p
2. Dömling A., Ugi I., Multicomponent reactions with isocyanides. Angewandte Chemie 2000 39 18 3169 3210 2-s2.0-2542509173
3. Kappe C. O., Recent advances in the Biginelli dihydropyrimidine synthesis. New tricks from an old dog. Accounts of Chemical Research 2000 33 12 879 888 2-s2.0-0034518876 10.1021/ar000048h (Pubitemid 32056773)
4. Vasuki G., Kumaravel K., Rapid four-component reactions in water: synthesis of pyranopyrazoles. Tetrahedron Letters 2008 49 39 5636 5638 2-s2.0-49149108373 10.1016/j.tetlet.2008.07.055
5. Al-Matar H. M., Khalil K. D., Adam A. Y., Elnagdi M. H., Green one pot solvent-free synthesis of pyrano[2,3- c ]-pyrazoles and pyrazolo[1,5-a] pyrimidines. Molecules 2010 15 9 6619 6629 2-s2.0-77957302251 10.3390/molecules15096619
6. Kanagaraj K., Pitchumani K., Solvent-free multicomponent synthesis of pyranopyrazoles: per-6-amino- β -cyclodextrin as a remarkable catalyst and host. Tetrahedron Letters 2010 51 25 3312 3316 2-s2.0-77953121188 10.1016/j.tetlet.2010.04.087
7. 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 Chemistry 2006 8 6 573 575 2-s2.0-33744955286 10.1039/b601209d (Pubitemid 43856614)
8. Wang J. L., Liu D., Zhang Z. J., Shan S., Han X., Srinivasula S. M., Croce C. M., Alnemri E. S., Huang Z., Structure-based discovery of an organic compound that binds Bcl-2 protein and induces apoptosis of tumor cells. Proceedings of the National Academy of Sciences of the United States of America 2000 97 13 7124 7129 2-s2.0-0034691130 10.1073/pnas.97.13.7124 (Pubitemid 30431428)
9. Zaki M. E. A., Soliman H. A., Hiekal O. A., Rashad A. E., Pyrazolopyranopyrimidines as a class of anti-inflammatory agents. Zeitschrift für Naturforschung C 2006 61 1-2 1 5 2-s2.0-33645057198
10. El-Tamany E. S. H., El-Shahed F. A., Mohamed B. H., Synthesis and biological activity of some pyrazole derivatives. Journal of the Serbian Chemical Society 1999 64 1 9 18 2-s2.0-0038936808
11. Kuo S. C., Huang L. J., Nakamura H., Studies on heterocyclic compounds. 6. Synthesis and analgesic and antiinflammatory activities of 3,4-dimethylpyrano[2,3- c ]pyrazol-6-one derivatives. Journal of Medicinal Chemistry 1984 27 4 539 544 2-s2.0-0021270880 (Pubitemid 14133746)
12. 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. Bioorganic and Medicinal Chemistry 2006 14 14 4792 4802 2-s2.0-33747254345 10.1016/j.bmc.2006.03.021
13. Junek H., Aigner H., Syntheses with nitriles. XXXV. Reactions of tetracyanoethylene with heterocycles. Chemische Berichte 1973 106 3 914 921
14. 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. Journal of Combinatorial Chemistry 2009 11 5 914 919 2-s2.0-70349330699 10.1021/cc900076j
15. Lehmann F., Holm M., Laufer S., Three-component combinatorial synthesis of novel dihydropyrano[2,3- c ] pyrazoles. Journal of Combinatorial Chemistry 2008 10 3 364 367 2-s2.0-45149110706 10.1021/cc800028m
16. Muramulla S., Zhao C.-G., A new catalytic mode of the modularly designed organocatalysts (MDOs): enantioselective synthesis of dihydropyrano[2,3- c ]pyrazoles. Tetrahedron Letters 2011 52 30 3905 3908 2-s2.0-79959520911 10.1016/j.tetlet.2011.05.092
17. Gogoi S., Zhao C.-G., Organocatalyzed enantioselective synthesis of 6-amino-5-cyanodihydropyrano[2,3- c ]pyrazoles. Tetrahedron Letters 2009 50 19 2252 2255 2-s2.0-62749200992 10.1016/j.tetlet.2009.02.210
18. Mecadon H., Rohman M. R., Kharbangar I., Laloo B. M., Kharkongor I., Rajbangshi M., Myrboh B., L-Proline as an efficicent catalyst for the multi-component synthesis of 6-amino-4-alkyl/aryl-3-methyl-2,4-dihydropyrano[2, 3- c ]pyrazole-5-carbonitriles in water. Tetrahedron Letters 2011 52 25 3228 3231 2-s2.0-79956214376 10.1016/j.tetlet.2011.04.048
19. Mecadon H., Rohman M. R., Rajbangshi M., Myrboh B., γ-Alumina as a recyclable catalyst for the four-component synthesis of 6-amino-4-alkyl/aryl-3- methyl-2,4-dihydropyrano[2,3- c ]pyrazole-5- carbonitriles in aqueous medium. Tetrahedron Letters 2011 52 19 2523 2525 2-s2.0-79953704828 10.1016/j.tetlet. 2011.03.036
20. Zou Y., Wu H., Hu Y., Liu H., Zhao X., Ji H., Shi D., A novel and environment-friendly method for preparing dihydropyrano[2,3- c ] pyrazoles in water under ultrasound irradiation. Ultrasonics Sonochemistry 2011 18 3 708 712 2-s2.0-79751536505 10.1016/j.ultsonch.2010.11.012
21. Nagarajan A. S., Reddy B. S. R., Synthesis of substituted pyranopyrazoles under neat conditions via a multicomponent reaction. Synlett 2009 12 2002 2004 2-s2.0-67651233213 10.1055/s-0029-1217526
22. Bihani M., Bora P. P., Bez G., Askari H., Mechanochemistry (grinding): an efficient route to synthesize of 6-amino-4 alkyl/aryl-3-methyl-2, 4-dihydropyrano[2, 3-c]pyrazole-carbonitrile. Oraganic Chemistry: An Indian Journal 2012 8 7 245 247
23. Narayan S., Muldoon J., Finn M. G., Fokin V. V., Kolb H. C., Sharpless K. B., 'On water': unique reactivity of organic compounds in aqueous suspension. Angewandte Chemie, International Edition 2005 44 21 3275 3279 2-s2.0-20344388819 10.1002/anie.200462883 (Pubitemid 40778352)
24. Narayan S., Lindström W. M., Organic Reactions in Water: Principles, Strategies and Applications 2007 1st Oxford, UK Blackwell Publishing
25. Chanda A., Fokin V. V., Organic synthesis 'on water' Chemical Reviews 2009 109 2 725 748 2-s2.0-64549117824 10.1021/cr800448q
26. Li C.-J., Organic reactions in aqueous media with a focus on carbon-carbon bond formations: a decade update. Chemical Reviews 2005 105 8 3095 3165 2-s2.0-24044470646 10.1021/cr030009u (Pubitemid 41222792)
27. Klijn J. E., Engberts J. B. F. N., Organic chemistry: fast reactions 'on water' Nature 2005 435 7043 746 747 2-s2.0-20544474189 10.1038/435746a (Pubitemid 40839711)
28. Hayashi Y., In water or in the presence of water? Angewandte Chemie, International Edition 2006 45 48 8103 8104 2-s2.0-33845788846 10.1002/anie.200603378 (Pubitemid 44974141)
29. Butler R. N., Coyne A. G., Water: nature's reaction enforcer-comparative effects for organic synthesis in-water and 'on-water' Chemical Reviews 2010 110 10 6302 6337 2-s2.0-77958060431 10.1021/cr100162c
30. Li C.-J., Chan T. H., Comprehensive Organic Reactions in Aqueous Media 2007 New York, NY, USA John Weily & Sons
31. Li C.-J., Chan T. H., Organic syntheses using indium-mediated and catalyzed reactions in aqueousmedia. Tetrahedron 1999 55 37 11149 11176 2-s2.0-0033543497 10.1016/S0040-4020(99)00641-9 (Pubitemid 29400730)
32. Pétrier C., Luche J. L., Allylzinc reagent additions in aqueous media. Journal of Organic Chemistry 1985 50 6 910 912 2-s2.0-33845377368
33. Sato A., Ito H., Taguchi T., Reaction of γ γ -dialkoxyallylic zirconium species with aldehyde as protected acryloyl anion. Journal of Organic Chemistry 2000 65 3 918 921 2-s2.0-0033960569 10.1021/jo991107b (Pubitemid 30091404)
34. Chan T. H., Yang Y., Indium-mediated organometallic reactions in aqueous media: the nature of the allylindium intermediate. Journal of the American Chemical Society 1999 121 13 3228 3229 2-s2.0-0001310676 10.1021/ja984359n (Pubitemid 29189775)
35. Wang Z., Yuan S., Li C.-J., Gallium-mediated allylation of carbonyl compounds in water. Tetrahedron Letters 2002 43 29 5097 5099 2-s2.0-0037100030 10.1016/S0040-4039(02)00995-4 (Pubitemid 34686875)
36. Chan T. C., Lau C. P., Chan T. H., Iron-mediated allylation of aryl aldehydes in aqueous media. Tetrahedron Letters 2004 45 21 4189 4191 2-s2.0-2342525330 10.1016/j.tetlet.2004.03.163 (Pubitemid 38581842)
37. Tan K. T., Cheng S. S., Cheng H. S., Loh T. P., Development of a highly α -regioselective metal-mediated allylation reaction in aqueous media: new mechanistic proposal for the origin of α -homoallylic alcohols. Journal of the American Chemical Society 2003 125 10 2958 2963 2-s2.0-0037433608 10.1021/ja029276s (Pubitemid 36512521)
38. Wang Z., Zha Z., Zhou C., Application of tin and nanometer tin in allylation of carbonyl compounds in tap water. Organic Letters 2002 4 10 1683 1685 2-s2.0-0037118363 10.1021/ol0257326
39. Otto S., Boccaleti G., Engberts J. B. F. N., A chiral lewis-acid-catalyzed Diels-Alder reaction. Water-enhanced enantioselectivity. Journal of the American Chemical Society 1998 120 4238 4239 2-s2.0-0033612740
40. Kobayashi S., Manabe K., Development of novel Lewis acid catalysts for selective organic reactions in aqueous media. Accounts of Chemical Research 2002 35 4 209 217 2-s2.0-0036105107 10.1021/ar000145a
41. Lindström U. M., Stereoselective organic reactions in water. Chemical Reviews 2002 102 8 2751 2772 2-s2.0-0036703508 10.1021/cr010122p (Pubitemid 35377630)
42. Pan C., Wang Z.Y., Catalytic asymmetric formation of carbon-carbon bond in the presence of water. Coordination Chemistry Reviews 2008 252 5-7 736 750 2-s2.0-39649102559 10.1016/j.ccr.2007.12.006
43. Marcus Y., Effect of ions on the structure of water: structure making and breaking. Chemical Reviews 2009 109 3 1346 1370 2-s2.0-65349131484 10.1021/cr8003828
44. Li C.-J., Organic reactions in aqueous media - with a focus on carbon-carbon bond formation. Chemical Reviews 1993 93 6 2023 2035 2-s2.0-0000677232
45. NIST Chemistry WebBook, Linstrom P. J., Mallard W. G.,. NIST Standard Reference Database Number 69, March, National Institute of Standards and Technology, Gaithersburg MD, 20899, 2003, http://webbook.nist.gov
46. Breslow R., Hydrophobic effects on simple organic reactions in water. Accounts of Chemical Research 1991 24 6 159 164 2-s2.0-12044255058
47. Akiya N., Savage P. E., Roles of water for chemical reactions in high-temperature water. Chemical Reviews 2002 102 8 2725 2750 2-s2.0-0036703742 10.1021/cr000668w (Pubitemid 35381647)