How to cite this paper
Khalili, B & Rimaz, M. (2014). Ultrasound-promoted synthesis of (4 or 5)-aryl-2-aryloyl-(1H)-imidazoles in water.Current Chemistry Letters, 3(1), 49-56.
Refrences
1. (a) Faulkner D. J. (2000) Marine natural products. Nat. Prod. Rep., 17, 7-55. (b) Ho J. Z., Hohareb R. M., Ahn J. H., Sim T. B., Rapoport H. (2003) Enantiospecific Synthesis of Carbapentostatins. J. Org. Chem., 68, 109-114.
2. Grimmett M. R., Katritsky A. R., Scriven E. F. V. (1996) Comprehensive Heterocycli Chemistry II, Eds. Pergamon: Oxford, Vol. 3, 77–220.
3. Domanska U., Kozlowska M. K. (2003) Solubility of imidazoles in ketones. Fluid Phase Equilib., 206, 253-266.
4. Maier T., Schmierer R., Bauer K., Bieringer H., Buerstell H., Sachser B. (1983) German Patent, 317094.
5. Schmierer R., Mildenberger H., Buerstell H. (1988) Chem. Abstr., 108, 37838.
6. Lo Y. S., Nolan J. C., Maren T. H., Welstead W. J. J., Gripshover D. F., Shamblee D. A. (1992) Synthesis and physiochemical properties of sulfamate derivatives as topical antiglaucoma agents. J. Med. Chem., 35, 4790-4794.
7. Lantos I., Zanng W. Y., Shiu Y., Eggleston D. S. (1993) Synthesis of imidazoles via hetero-Cope rearrangements. J. Org. Chem., 58, 7092-7095.
8. Zhang C., Moran E. J., Woiwade T. F., Short K. M., Mjalli A. M. M. (1996) Synthesis of tetrasubstituted imidazoles via ?-(N-acyl-N-alkylamino)-B-ketoamides on Wang resin. Tetrahedron Lett., 37, 751-754.
9. Mason T. J. (2007) Sonochemistry and the environment-providing a “green” link between chemistry, physics and engineering. Ultrason. Sonochem., 14, 476-483.
10. Mason T. J. (1991) Practical Sonochemistry., Ellis Horwood, 18.
11. (a) Mason T. J., and Peters D. (2002) Practical Sonochemistry. Second Ed., Ellis Horwood, London. (b) Luche J. L. (1998) Synthetic Organic Sonochemistry. Plenum, New York. (c) Mason T. J., and Lorimer J. P. (1988) Sonochemistry: Theory, Applications and Uses of Ultrasound in Chemistry. Ellis Horwood, Chichester.
12. (a) Eftekhari-Sis B., Zirak M., Akbari A. (2013) Arylglyoxals in synthesis of heterocyclic compounds. Chem. Rev., 113, 2958-3043. (b) Akbari A. (2012) Phenylglyoxal. Synlett, 23, 951-952. (c) Khalili B., Jajarmi P., Eftekhari- Sis B., and Hashemi M. M. (2008) Novel one-pot, three-component synthesis of new 2-alkyl-5- aryl-(1H)-pyrrole-4-ol in water. J. Org. Chem., 73, 2090-2095. (d) Khalili B., Tondro T., Hashemi M. M. (2009) Novel one-pot synthesis of (4 or 5)-aryloyl-(1H)-imidazoles in water and tauto-isomerization study using NMR. Tetrahedron, 65, 6882-6887. (e) Rimaz M., and Khalafy J. (2010) Novel one-pot, three component synthesis of alkyl 6-aryl-3-methylpyridazine-4-carboxylates in water. Arkivoc, ii, 110-117. (f) Rimaz M., Khalafy J., Najafi Moghadam, P. (2010) A Regioselective One-Pot, Three Component Synthesis of 6-Aryl-4-cyano-3(2H)-pyridazinones in Water. Aust. J. Chem, 63, 1396-1401. (g) Rimaz M., Khalafy J., Noroozi Pesyan N., Prager R. H. (2010) A Simple One-Pot, Three Component Synthesis of 3-Arylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-diones and their Sulfur Analogues as Potential Monoamine Oxidase Inhibitors. Aust. J. Chem., 63, 507-510. (h) Khalafy J., Poursattar Marjani A., Haghipour M. (2013) Regioselective synthesis of 3-arylpyrido[2,3-b]pyrazines by reaction of arylglyoxals with 2,3-diaminopyridine. Curr. Chem. Lett., 2 (1), 21-26. (i) Eftekhari-Sis B., Vahdati-Khajeh, S. (2013) Ultrasound-assisted green synthesis of pyrroles and pyridazines in water via three-component condensation reactions of arylglyoxals., Curr. Chem. Lett., 2, 85-92.
13. Riley H. A., Gray A. R. (1943) Phenylglyoxal. Organic Syntheses, Wiley & Sons: New York, NY, Collect. Vol. II, p 509.
14. Schmidt M. W., Baldridge K. K., Boatz J. A., Elbert S. T., Gordon M. S., Jensen J. H., Koseki S., Matsunaga N., Nguyen K. A., Su S. J., Windus T. L., Dupuis M. and Montgomery J. A. (1993) General atomic and molecular electronic structure system, J. Comput. Chem., 14, 1347-1363.
15. Foresman J. B. and Frisch A. E. (1998) Exploring chemistry with electronic structure methods, Gaussian Inc., Pittsburgh, PA,.
16. Frisch M. J., Trucks G. W., Schlegel H. B., Scuseria G. E., Robb M. A., Cheeseman J. R., Montgomery J. A., Vreven T., Kudin K. N., Burant J. C., Millam J. M., Iyengar S. S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G. A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J. E., Hratchian H. P., Cross J. B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R. E., Yazyev O., Austin A. J., Cammi R., Pomelli C., Ochterski J. W., Ayala P. Y., Morokuma K., Voth G. A., Salvador P., Dannenberg J. J., Zakrzewski V. G., Dapprich S., Daniels A. D., Strain M. C., Farkas O., Malick D. K., Rabuck A. D., Raghavachari K., Foresman J. B., Ortiz J. V., Cui Q., Baboul A. G., Clifford S., Cioslowski J., Stefanov B. B., Liu G., Liashenko A., Piskorz I., Komaromi R. L., Martin D. J., Fox T., Keith M. A., Al-Laham C. Y., Peng A., Nanayakkara P., Challacombe M., Gill P. M. W., Johnson B., Chen W., Wong M. W., Gonzalez C. and Pople J. A. Gaussian 03, Revision C.02, Gaussian Inc., Wallingford CT, (2004).
17. Marino T., Russo N. and Toscano M. (2000) Gas-phase metal ion (Li+, Na+, Cu+) affinities of glycine and alanine, J. Inorg. Biochem., 79, 179-185.
18. Hoyau S. and Ohanessian G. (1998) Interaction of Alkali Metal Cations (Li+-Cs+) with Glycine in the Gas Phase: A Theoretical Study, Chem. Eur. J., 4, 1561-1569.
19. Bertran J., Rodriguez-Santiago L. and Sodupe M. (1999) The different nature of bonding in Cu+-glycine and Cu++-glysine, J. Phys. Chem. B, 103, 2310-2317.
20. Spartan 06V102, Wavefunction, Inc., Irvine, CA.
21. Becke A. D. (1993) Densityfunctional thermochemistry. III. The role of exact exchange, J. Chem. Phys., 98, 5648-5652.
22. Lee C., Yang W. and Parr R. G. (1998) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density, Phys. Rev. B, 37, 785-789 .
2. Grimmett M. R., Katritsky A. R., Scriven E. F. V. (1996) Comprehensive Heterocycli Chemistry II, Eds. Pergamon: Oxford, Vol. 3, 77–220.
3. Domanska U., Kozlowska M. K. (2003) Solubility of imidazoles in ketones. Fluid Phase Equilib., 206, 253-266.
4. Maier T., Schmierer R., Bauer K., Bieringer H., Buerstell H., Sachser B. (1983) German Patent, 317094.
5. Schmierer R., Mildenberger H., Buerstell H. (1988) Chem. Abstr., 108, 37838.
6. Lo Y. S., Nolan J. C., Maren T. H., Welstead W. J. J., Gripshover D. F., Shamblee D. A. (1992) Synthesis and physiochemical properties of sulfamate derivatives as topical antiglaucoma agents. J. Med. Chem., 35, 4790-4794.
7. Lantos I., Zanng W. Y., Shiu Y., Eggleston D. S. (1993) Synthesis of imidazoles via hetero-Cope rearrangements. J. Org. Chem., 58, 7092-7095.
8. Zhang C., Moran E. J., Woiwade T. F., Short K. M., Mjalli A. M. M. (1996) Synthesis of tetrasubstituted imidazoles via ?-(N-acyl-N-alkylamino)-B-ketoamides on Wang resin. Tetrahedron Lett., 37, 751-754.
9. Mason T. J. (2007) Sonochemistry and the environment-providing a “green” link between chemistry, physics and engineering. Ultrason. Sonochem., 14, 476-483.
10. Mason T. J. (1991) Practical Sonochemistry., Ellis Horwood, 18.
11. (a) Mason T. J., and Peters D. (2002) Practical Sonochemistry. Second Ed., Ellis Horwood, London. (b) Luche J. L. (1998) Synthetic Organic Sonochemistry. Plenum, New York. (c) Mason T. J., and Lorimer J. P. (1988) Sonochemistry: Theory, Applications and Uses of Ultrasound in Chemistry. Ellis Horwood, Chichester.
12. (a) Eftekhari-Sis B., Zirak M., Akbari A. (2013) Arylglyoxals in synthesis of heterocyclic compounds. Chem. Rev., 113, 2958-3043. (b) Akbari A. (2012) Phenylglyoxal. Synlett, 23, 951-952. (c) Khalili B., Jajarmi P., Eftekhari- Sis B., and Hashemi M. M. (2008) Novel one-pot, three-component synthesis of new 2-alkyl-5- aryl-(1H)-pyrrole-4-ol in water. J. Org. Chem., 73, 2090-2095. (d) Khalili B., Tondro T., Hashemi M. M. (2009) Novel one-pot synthesis of (4 or 5)-aryloyl-(1H)-imidazoles in water and tauto-isomerization study using NMR. Tetrahedron, 65, 6882-6887. (e) Rimaz M., and Khalafy J. (2010) Novel one-pot, three component synthesis of alkyl 6-aryl-3-methylpyridazine-4-carboxylates in water. Arkivoc, ii, 110-117. (f) Rimaz M., Khalafy J., Najafi Moghadam, P. (2010) A Regioselective One-Pot, Three Component Synthesis of 6-Aryl-4-cyano-3(2H)-pyridazinones in Water. Aust. J. Chem, 63, 1396-1401. (g) Rimaz M., Khalafy J., Noroozi Pesyan N., Prager R. H. (2010) A Simple One-Pot, Three Component Synthesis of 3-Arylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-diones and their Sulfur Analogues as Potential Monoamine Oxidase Inhibitors. Aust. J. Chem., 63, 507-510. (h) Khalafy J., Poursattar Marjani A., Haghipour M. (2013) Regioselective synthesis of 3-arylpyrido[2,3-b]pyrazines by reaction of arylglyoxals with 2,3-diaminopyridine. Curr. Chem. Lett., 2 (1), 21-26. (i) Eftekhari-Sis B., Vahdati-Khajeh, S. (2013) Ultrasound-assisted green synthesis of pyrroles and pyridazines in water via three-component condensation reactions of arylglyoxals., Curr. Chem. Lett., 2, 85-92.
13. Riley H. A., Gray A. R. (1943) Phenylglyoxal. Organic Syntheses, Wiley & Sons: New York, NY, Collect. Vol. II, p 509.
14. Schmidt M. W., Baldridge K. K., Boatz J. A., Elbert S. T., Gordon M. S., Jensen J. H., Koseki S., Matsunaga N., Nguyen K. A., Su S. J., Windus T. L., Dupuis M. and Montgomery J. A. (1993) General atomic and molecular electronic structure system, J. Comput. Chem., 14, 1347-1363.
15. Foresman J. B. and Frisch A. E. (1998) Exploring chemistry with electronic structure methods, Gaussian Inc., Pittsburgh, PA,.
16. Frisch M. J., Trucks G. W., Schlegel H. B., Scuseria G. E., Robb M. A., Cheeseman J. R., Montgomery J. A., Vreven T., Kudin K. N., Burant J. C., Millam J. M., Iyengar S. S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G. A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J. E., Hratchian H. P., Cross J. B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R. E., Yazyev O., Austin A. J., Cammi R., Pomelli C., Ochterski J. W., Ayala P. Y., Morokuma K., Voth G. A., Salvador P., Dannenberg J. J., Zakrzewski V. G., Dapprich S., Daniels A. D., Strain M. C., Farkas O., Malick D. K., Rabuck A. D., Raghavachari K., Foresman J. B., Ortiz J. V., Cui Q., Baboul A. G., Clifford S., Cioslowski J., Stefanov B. B., Liu G., Liashenko A., Piskorz I., Komaromi R. L., Martin D. J., Fox T., Keith M. A., Al-Laham C. Y., Peng A., Nanayakkara P., Challacombe M., Gill P. M. W., Johnson B., Chen W., Wong M. W., Gonzalez C. and Pople J. A. Gaussian 03, Revision C.02, Gaussian Inc., Wallingford CT, (2004).
17. Marino T., Russo N. and Toscano M. (2000) Gas-phase metal ion (Li+, Na+, Cu+) affinities of glycine and alanine, J. Inorg. Biochem., 79, 179-185.
18. Hoyau S. and Ohanessian G. (1998) Interaction of Alkali Metal Cations (Li+-Cs+) with Glycine in the Gas Phase: A Theoretical Study, Chem. Eur. J., 4, 1561-1569.
19. Bertran J., Rodriguez-Santiago L. and Sodupe M. (1999) The different nature of bonding in Cu+-glycine and Cu++-glysine, J. Phys. Chem. B, 103, 2310-2317.
20. Spartan 06V102, Wavefunction, Inc., Irvine, CA.
21. Becke A. D. (1993) Densityfunctional thermochemistry. III. The role of exact exchange, J. Chem. Phys., 98, 5648-5652.
22. Lee C., Yang W. and Parr R. G. (1998) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density, Phys. Rev. B, 37, 785-789 .