One-pot process to Z-α-benzoylamino-acrylic acid methyl esters via potassium phosphate-catalyzed Erlenmeyer reaction

Tetrahedron Letters

Volumn 51, Issue 4, 2010, Pages 625-628

  Cleary, Thomas ^a   Brice, Jodie ^a   Kennedy, Nicole ^a   Chavez, Flavio ^a  

^a Roche Carolina   (United States)

Author keywords

Acrylic acids; Erlenmeyer reaction; Oxazolones

Indexed keywords

ACRYLIC ACID METHYL ESTER; ALDEHYDE; HIPPURIC ACID; OXAZOLONE; POTASSIUM DIHYDROGEN PHOSPHATE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; METHANOLYSIS; ONE POT SYNTHESIS; RING OPENING;

EID: 72149092940     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.11.081     Document Type: Article

References (22)

1. Aguado G.P., Monglioni A.G., and Ortuño R.M. Tetrahedron: Asymmetry 14 (2003) 217-223
2. Marino S.T., Stachurska-Buczek D., Huggins B.M., Krywult B.M., Sheehan C.S., Nguyen T., Choi N., Parson J.G., Griffiths P.G., James I.W., Bray A.M., White J.M., and Boyce R.S. Molecules 9 (2004) 405-426
3. Zhang F.Y., Kwok W.H., and Chan A.S.C. Tetrahedron: Asymmetry 12 (2001) 2337-2342
4. Plöchl J. Ber. 16 (1893) 2815 Ber. 1884, 17, 1616
5. Erlenmeyer E. Ann (1893) 275
6. Li J.J. Name Reactions in Heterocyclic Chemistry (2005), John Wiley & Sons, New Jersey pp 229-233
7. Rao Y.S. J. Org. Chem. 41 (1976) 722-725
8. Rao Y.S., and Filler R. Synthesis (1975) 749-764
9. Kennedy, N.; Cleary, T.; Rawalpally, T.; Chavez, F. Substituent Effect on the Erlenmeyer Plochl Reaction; Understanding an Observed Process Reaction Time; in press.
10. Karade N.N., Shirodkar S.G., Dhoot B.M., and Waghmare P.B. J. Chem. Res. (2005) 46-47
11. Yu C., Zhou B., Su W., and Xu Z. Synth. Commun. 36 (2006) 3447-3453
12. Päsha M.A., Jayäshankara V.P., Venugopala K.N., and Rao G.K. J. Pharmacol. Toxicol. 2 (2007) 264-270
13. Tikdari A.M., Fozooni S., and Hamidian H. Molecules 13 (2008) 3246-3252
14. Heravi M.R. J. Univ. Chem. Technol. Metall. 44 (2009) 86-90
15. Fennoy L.V. J. Org. Chem. 26 (1961) 4696-4698
16. addition-rise = 41.7 °C.
17. Krause H.W., Taudien S., and Schinkowski K. Tetrahedron: Asymmetry 4 (1993) 73-84
18. Selke R., Facklam C., and Heller D. Tetrahedron: Asymmetry 4 (1993) 369-382
19. Krause H.W., Wilcke F.W., Kreuzfeld H.J., and Döbler CH. Chirality 4 (1992) 110-115
20. Arenal I., Bernabe M., and Alvarez E. An. Quim. 77 (1981) 56
21. 13C NMR, and melting point for purity.
22. 6): δ 165.62, 165.07, 149.16, 145.61, 133.42, 131,83, 128.47, 127.68, 123.31, 120.84, 116.04, 112.54, 52.20.