GSC  Vol.1 No.4 , November 2011
Solar Thermochemical Reactions IV: Unusual Reaction of Nitrones with Acetonitrile Derivatives Induced by Solar Thermal Energy
ABSTRACT
The behaviour of cyanothioacetamide 1 and the acetonitrile derivatives 6 and 10, respectively, towards the nitrones 2a-i induced by free solar thermal energy is reported. Structures and reaction mechanisms are also discussed.

Cite this paper
nullR. Mekheimer, K. Al-Zaydi, A. Al-Shamary and K. Sadek, "Solar Thermochemical Reactions IV: Unusual Reaction of Nitrones with Acetonitrile Derivatives Induced by Solar Thermal Energy," Green and Sustainable Chemistry, Vol. 1 No. 4, 2011, pp. 176-181. doi: 10.4236/gsc.2011.14027.
References
[1]   P. Merino, “Science of Synthesis,” In: A. Padwa, D. Bellus, Eds., George-Thieme Verlag, Stuttgart, Vol. 27, 2004, p. 511.

[2]   J. J. Tufariello, “1,3-Dipolar Cycloaddition Chemistry,” In: A. Padwa, Ed., Wiley, New York, Vol. 2, 1984, p. 83.

[3]   A. Padwa and A. M. Schoffstall, “Advances in Cycloaddition,” In: D. P. Curran, Ed., JAI Press, Greenwich, Vol. 2, 1990, p. 2.

[4]   A. Padwa, “Synthetic Applications of 1, 3-Dipolar Cy- cloaddition Chemistry toward Heterocycles and Natural Products,” In: W. H. Pearson, Ed., Wiley and Sons, Ho- boken, 2003, pp. 1-83.

[5]   K. V. Gothelf and K. A. J?rgensen, “Asymmetric 1,3- Dipolar cycloaddition Reactions,” Chemical Reviews, Vol. 98, No. 2, 1998, pp. 863-910. doi:10.1021/cr970324e

[6]   M. Frederickson, “Optically Active Isoxazolidines via A- symmetric Cycloaddition Reactions of Nitrones with Al- kenes: Applications in Organic Synthesis,” Tetrahedron, Vol. 53, No. 2, 1997, pp. 403-425. doi:10.1016/S0040-4020(96)01095-2

[7]   J. J. Tufariello, “1, 3-Dipolar Cycloaddition Chemistry,” In: A. Padwa, Ed., Wiley and Sons, New York, 1984, pp. 83-167.

[8]   U. Chiacchio, A. Rescifina, G. Romeo and O. A. Attanasi, “Targets in Heterocyclic Systems,” In: D. Spinelli, Ed., Italian Society of Chemistry, Rome, Vol. 1, 1997, p. 225.

[9]   P. Merino, S. Franco, F. L. Merchan and T. Tejero, “Nucleophilic Additions to Chiral Nitrones: New Approaches to Nitrogenated Compounds,” Synlett, Vol. 2000, No. 4, 2000, pp. 442-454. doi:10.1055/s-2000-6555

[10]   M. Lombardo and C. Trombini, “Nucleophilic Additions to Nitrones,” Synthesis, No. 6, 2000, pp. 759-774. doi:10.1055/s-2000-6269

[11]   P. Merino, “New Developments in Nucleophilic Additions to Nitrones,” Comptes Rendus Chimie, Vol. 8, No. 5, 2005, pp. 775-788. doi:10.1016/j.crci.2005.02.013

[12]   R. A. Mekheimer, A. M. Abdel Hameed and K. U. Sadek, “Solar Thermochemical Reactions: Four-Component Synthesis of Polyhydroquinoline Derivatives Induced by Solar Thermal Energy,” Green Chemistry, Vol. 10, No. 5, 2008, pp. 592-593. doi:10.1039/b715126h

[13]   R. A. Mekheimer, M. A. Ameen and K. U. Sadek, “Solar Thermochemical Reactions II: Synthesis of 2-Amino- Thiophenes via Gewald Reaction Induced by Solar Ther- mal Energy,” Chinese Chemical Letters, Vol. 19, No. 7, 2008, pp. 788-790. doi:10.1016/j.cclet.2008.04.041

[14]   R. A. Mekheimer, A. M. Abdel Hameed, S. A. A. Mansour and K. U. Sadek, “Solar Thermochemical Reactions III: A Convenient One-Pot Synthesis of 1,2,4,5-Tetra- substituted Imidazoles Ccatalyzed by High Surface Area SiO2 and Induced by Solar Thermal Energy,” Chinese Chemical Letters, Vol. 20, 2009, pp. 812-814. doi:10.1016/j.cclet.2009.02.017

[15]   J. S. A. Brunskill, A. De and D. F. Ewing, “Dimerisation of 3-Aryl-2-cyanothioacrylamides. A [2s+4s] Cycloaddition to give Substituted 3,4-Dihydro-2H-thiopyrans,” Jour- nal of the Chemical Society, Perkin Transactions, Vol. 1, 1978, 629-633.

[16]   V. G. Brunton, M. J. Lear, D. J. Robins, S. Williamson and P. Workman, “Synthesis and Antiproliferative Activity of Tyrphostins Containing Heteroaromatic Moieties,” Anti-Cancer Drug Design, Vol. 9, No. 4, 1994, p. 291- 309.

[17]   B. Tornetta, G. Scapini, F. Guerrera and A. Bernardini, “Structure-Antibacterial Activity Relations of Arylthio- amides. IV. Synthesis, UV Spectra and Tuberculostatic Activity in vitro of Some Arylvinylenethioamides,” Boll. Seduta Accad. Gioenia Sci. Nat. Catania, Vol. 10, No. 5, 1970, pp. 353-363.

[18]   V. Grinstein and L. Serina, “Cyanothioacetamide and Its Derivatives,” Latvijas P. S. R. Zinatnu Akad. Vestis, Kim. Ser, Vol. 4, 1963, pp. 469-474.

[19]   R. A. Mekheimer and R. M. Shaker, “Synthesis and Reactivity of 3-Alkylthio-5-Cyanomethyl-4-Phenyl-1,2,4-tri- azoles”, Journal of Chemical Research, No. 2, 1999, pp. 76-77. doi:10.1039/a806842i

[20]   K. Saito, S. Kambe, Y. Nakano, A. Sakurai and H. Midorikawa, “Synthetic Studies Using ?, β-Unsa- turated Nitriles: A Convenient Preparation of 1,3- Benzothiazole Derivatives,” Synthesis, No. 3, 1983, pp. 210-212. doi:10.1055/s-1983-30284

 
 
Top