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The Scientific World Journal
Volume 2014, Article ID 634935, 10 pages
http://dx.doi.org/10.1155/2014/634935
Research Article

A Novel One-Pot and One-Step Microwave-Assisted Cyclization-Methylation Reaction of Amino Alcohols and Acetylated Derivatives with Dimethyl Carbonate and TBAC

1Centro de Graduados e Investigación en Química del Instituto Tecnológico de Tijuana, Boulevard Alberto Limón Padilla S/N 22510 Tijuana, BC, Mexico
2Área de Ciencias Básicas e Ingenierías, Universidad Autónoma de Nayarit, Cd. de la Cultura Amado Nervo S/N 63190 Tepic, Nay, Mexico

Received 12 April 2014; Revised 19 August 2014; Accepted 20 August 2014; Published 14 October 2014

Academic Editor: Antal Tungler

Copyright © 2014 Adrián Ochoa-Terán et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. A. I. Meyers, D. A. Dickman, and T. R. Bailey, “Asymmetric synthesis of 2-alkylpyrrolidines and piperidines. Synthesis of (+)-metazocine,” Journal of the American Chemical Society, vol. 107, no. 26, pp. 7974–7978, 1985. View at Publisher · View at Google Scholar · View at Scopus
  2. D. A. Dickman, A. I. Meyers, G. A. Smith, and R. E. Gawley, “Reduction of a-aminoacids: L-Valinol [1-Butanol, 2-amino-3-methyl-, (S)-],” Organic Syntheses, vol. 7, p. 530, 1990. View at Google Scholar
  3. J. R. Gage and D. A. Evans, “(S)-4-(phenylmethyl)-2-oxazolidinone [2-oxazolidinone, 4-(phenylmethyl)-,(S)-],” Organic Syntheses, vol. 68, pp. 77–80, 1990. View at Publisher · View at Google Scholar
  4. A. Abiko and S. Masamune, “An improved, convenient procedure for reduction of amino acids to aminoalcohols: use of NaBH4-H2SO4,” Tetrahedron Letters, vol. 33, no. 38, pp. 5517–5518, 1992. View at Publisher · View at Google Scholar · View at Scopus
  5. E. Nicolas, K. C. Russell, and V. J. Hruby, “Asymmetric 1,4-addition of organocuprates to chiral .alpha.,.beta.-unsaturated N-acyl-4-phenyl-2-oxazolidinones: a new approach to the synthesis of chiral .beta.-branched carboxylic acids,” The Journal of Organic Chemistry, vol. 58, pp. 766–770, 1993. View at Publisher · View at Google Scholar
  6. D. A. Quagliato, P. M. Andrae, and E. M. Matelan, “Efficient procedure for the reduction of α-amino acids to enantiomerically pure α-methylamines,” Journal of Organic Chemistry, vol. 65, no. 16, pp. 5037–5042, 2000. View at Publisher · View at Google Scholar · View at Scopus
  7. M. S. Newman and A. Kutner, “New reactions involving alkaline treatment of 3-nitroso-2-oxazolidones,” Journal of the American Chemical Society, vol. 73, no. 9, pp. 4199–4204, 1951. View at Publisher · View at Google Scholar · View at Scopus
  8. J. B. Hyne, “Nuclear magnetic resonance spectra and configuration. The n.m.r. spectra of diastereoisomeric heterocyclic derivatives of the ephedrines,” Journal of the American Chemical Society, vol. 81, no. 22, pp. 6058–6061, 1959. View at Publisher · View at Google Scholar · View at Scopus
  9. W. Lubell and H. Rapoport, “Surrogates for chiral aminomalondialdehyde. Synthesis of N-(9-phenylfluoren-9-yl)serinal and N-(9-phenylfluoren-9-yl)vinylglycinal,” Journal of Organic Chemistry, vol. 54, no. 16, pp. 3824–3831, 1989. View at Publisher · View at Google Scholar · View at Scopus
  10. J. M. Stratton and F. J. Wilson, “146. Some derivatives of d-nor-ψ-ephedrine,” Journal of the Chemical Society, pp. 1133–1138, 1932. View at Publisher · View at Google Scholar · View at Scopus
  11. W. J. Close, “The conformation of the ephedrines,” Journal of Organic Chemistry, vol. 15, no. 5, pp. 1131–1134, 1950. View at Publisher · View at Google Scholar · View at Scopus
  12. W. J. Close, “Anticonvulsant drugs. IV: some 2-oxazolidones,” Journal of the American Chemical Society, vol. 73, no. 1, pp. 95–98, 1951. View at Publisher · View at Google Scholar · View at Scopus
  13. C. Agami, F. Couty, L. Hamon, and O. Venier, “Chiral oxazolidinones from N-boc derivatives of β-amino alcohols. Effect of a N-methyl substituent on reactivity and stereoselectivity,” Tetrahedron Letters, vol. 34, no. 28, pp. 4509–4512, 1993. View at Publisher · View at Google Scholar · View at Scopus
  14. D. A. Evans and A. E. Weber, “Asymmetric glycine enolate aldol reactions: synthesis of cyclosporin's unusual amino acid, MeBmt,” Journal of the American Chemical Society, vol. 108, no. 21, pp. 6757–6761, 1986. View at Publisher · View at Google Scholar · View at Scopus
  15. M. G. Organ, Y. V. Bilokin, and S. Bratovanov, “Approach toward the total synthesis of orevactaene, 2: convergent and stereoselective synthesis of the C18-C31 domain of orevactaene: evidence for the relative configuration of the side chain,” Journal of Organic Chemistry, vol. 67, no. 15, pp. 5176–5183, 2002. View at Publisher · View at Google Scholar · View at Scopus
  16. C. A. Marques, M. Selva, P. Tundo, and F. Montanari, “Reaction of oximes with dimethyl carbonate: a new entry to 3-methyl-4,5-disubstituted-4-oxazolin-2-ones,” Journal of Organic Chemistry, vol. 58, no. 21, pp. 5765–5770, 1993. View at Publisher · View at Google Scholar · View at Scopus
  17. Y. Fu, T. Baba, and Y. Ono, “Carbonylation of o-phenylenediamine and o-aminophenol with dimethyl carbonate using lead compounds as catalysts,” Journal of Catalysis, vol. 197, no. 1, pp. 91–97, 2001. View at Publisher · View at Google Scholar · View at Scopus
  18. M. Selva, “The reaction of dialkyl carbonates with o-aminophenol catalysed by K 2CO3: a novel high-yield synthesis of N-alkylbenzoxazol-2- ones,” Synthesis, no. 18, pp. 2872–2876, 2003. View at Google Scholar · View at Scopus
  19. P. Wasserscheid and W. Keim, “Ionic liquids-new “solutions” for transition metal catalysis,” Angewandte Chemie International Edition, vol. 39, pp. 3772–3789, 2000. View at Google Scholar
  20. R. A. Brown, P. Pollet, E. McKoon, C. A. Eckert, C. L. Liotta, and P. G. Jessop, “Asymmetric hydrogenation and catalyst recycling using ionic liquid and supercritical carbon dioxide,” Journal of the American Chemical Society, vol. 123, no. 6, pp. 1254–1255, 2001. View at Publisher · View at Google Scholar · View at Scopus
  21. R. Sheldon, “Catalytic reactions in ionic liquids,” Chemical Communications, no. 23, pp. 2399–2407, 2001. View at Publisher · View at Google Scholar
  22. T. Sima, S. Guo, F. Shi, and Y. Deng, “The syntheses of carbamates from reactions of primary and secondary aliphatic amines with dimethyl carbonate in ionic liquids,” Tetrahedron Letters, vol. 43, no. 45, pp. 8145–8147, 2002. View at Publisher · View at Google Scholar · View at Scopus
  23. J. Mo, L. Xu, and J. Xiao, “Ionic liquid-promoted, highly regioselective heck arylation of electron-rich olefins by aryl halides,” Journal of the American Chemical Society, vol. 127, pp. 751–760, 2005. View at Publisher · View at Google Scholar
  24. J. Sun, S.-I. Fujita, and M. Arai, “Development in the green synthesis of cyclic carbonate from carbon dioxide using ionic liquids,” Journal of Organometallic Chemistry, vol. 690, no. 15, pp. 3490–3497, 2005. View at Publisher · View at Google Scholar · View at Scopus
  25. H.-Y. Ju, M. D. Manju, D.-W. Park, Y. Choe, and S.-W. Park, “Performance of ionic liquid as catalysts in the synthesis of dimethyl carbonate from ethylene carbonate and methanol,” Reaction Kinetics and Catalysis Letters, vol. 90, no. 1, pp. 3–9, 2007. View at Publisher · View at Google Scholar
  26. W.-C. Shieh, S. Dell, and O. Repič, “1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) and microwave-accelerated green chemistry in methylation of phenols, indoles, and benzimidazoles with dimethyl carbonate,” Organic Letters, vol. 3, pp. 4279–4281, 2001. View at Publisher · View at Google Scholar
  27. W.-C. Shieh, S. Dell, and O. Repič, “Large scale microwave-accelerated esterification of carboxylic acids with dimethyl carbonate,” Tetrahedron Letters, vol. 43, no. 32, pp. 5607–5609, 2002. View at Publisher · View at Google Scholar · View at Scopus
  28. R. Leticia Guerrero and I. A. Rivero, “1,2-Dimethylimidazole (DMI) and microwaves in the alkylation of carboxylic acids and phenols with dimethyl and diethyl carbonates,” Arkivoc, vol. 2008, no. 11, pp. 295–306, 2008. View at Publisher · View at Google Scholar · View at Scopus
  29. A. Pawelczyk and L. Zaprutko, “Microwave assisted synthesis of fragrant jasmone heterocyclic analogues,” European Journal of Medicinal Chemistry, vol. 41, pp. 586–591, 2006. View at Google Scholar
  30. G. R. Leticia and I. A. Rivero, “Reaction of o-aminobenzamides with dialkyl carbonates and ionic liquids: a novel one-pot, high-yield, microwave-assisted synthesis of 1-alkylquinazoline-2,4-diones,” Journal of the Mexican Chemical Society, vol. 56, no. 2, pp. 201–206, 2012. View at Google Scholar
  31. A. Ochoa-Terán and I. A. Rivero, “New synthesis of mephenoxalone,” Arkivoc, vol. 2008, no. 2, pp. 235–242, 2008. View at Google Scholar
  32. M. Selva, F. Trotta, and P. Tundo, “Esters and orthoesters as alkylating agents at high temperature. Applications to continuous-flow processes,” Journal of the Chemical Society, Perkin Transactions, vol. 2, pp. 519–522, 1992. View at Google Scholar
  33. M. Selva, C. A. Marques, and P. J. Tundo, “Selective mono-methylation of arylacetonitriles and methyl arylacetates by dimethylcarbonate,” Journal of the Chemical Society, Perkin Transactions, vol. 1, pp. 1323–1328, 1994. View at Google Scholar