Development of a one-pot method for the homologation of aldehydes to carboxylic acids

Tetrahedron

Volumn 65, Issue 37, 2009, Pages 7794-7800

  McNulty, James ^a   Das, Priyabrata ^a  

^a MCMASTER UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALPHA PHOSPHONOENAMINE; CARBON; CARBOXYLIC ACID; ENAMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROLYSIS; ONE POT SYNTHESIS; PRIORITY JOURNAL; STRUCTURAL HOMOLOGY;

EID: 68249103342     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.07.032     Document Type: Article

References (46)

1. Over 20 marketed pharmaceuticals are phenylacetic acid derivatives including diclofenac (anti-arthritic), ibufenac (anti-inflammatory), ritalin (anti-ADHD), homovanillic acid (schizophrenia), propanidid (anesthetic) guanfacine (antihypertensive), and 4-chlorophenylacetic acid (anti-neoplastic). For a selection of examples see:
2. Failli, A. A.; Kreft, A. F.; Musser, J. H. U.S. Patent 5,021,576, 1991;
3. Nahar L., Russel W.R., Middleton M., Shoeb M., and Sarker S.D. Acta Pharm. 55 (2005) 187-193
4. Santini C., Berger G.D., Han W., Mosley R., MacNaul K., Berger J., Doebber T., Wu M., Moller D.E., Tolman R.L., and Sahoo S.P. Bioorg. Med. Chem. Lett. 13 (2003) 1277-1280
5. Rakowitz D., Gmeiner A., Schroder N., and Matuszczak B. Eur. J. Pharm. Sci. 27 (2006) 188-193
6. Sidell N., Kirma N., Morgan E.T., Nair H., and Tekmal R.R. Cancer Lett. 251 (2007) 302-310
7. For a selection of synthetic applications see:
8. Gore M.P., and Vederas J.C. J. Org. Chem. 51 (1986) 3700-3704
9. Prashad M., Kim H.Y., Har D., Repic O., and Blacklock T.J. Tetrahedron Lett. 39 (1998) 9369-9372
10. Wittenberger S.J., and McLaughlin M.A. Tetrahedron Lett. 40 (1999) 7175-7178
11. Bull S.D., Davies S.G., Key M.S., Nicholson R.L., and Savory E.D. Chem. Commun. (2000) 1721-1722
12. McNulty J., Nair J.J., Sliwinski M., Harrington L.E., and Pandey S. Eur. J. Org. Chem. (2007) 5669-5673
13. McNulty J., Nair J.J., Pandey S., and Griffin C. J. Nat. Prod. 71 (2008) 357-363
14. Kohlpaintner C.W., and Beller M. J. Mol. Catal. A: Chem. 116 (1997) 259-267
15. Adams R., and Thal A.F. Org. Synth. 2 (1922) 9-11
16. Adams R., and Thal A.F. Org. Synth. 2 (1922) 27-28
17. Corey E.J., and Markl G. Tetrahedron Lett. 33 (1967) 3201-3204
18. Gross H., and Costisella B. Angew. Chem., Int. Ed. Engl. 7 (1968) 391-392
19. Schollkopf U., and Schroder R. Angew. Chem., Int. Ed. Engl. 11 (1972) 311-312
20. Jones P.F., and Lappert M.F. J. Chem. Soc., Chem. Commun. (1972) 526
21. White D.R., and Wu D.K. J. Chem. Soc., Chem. Commun. (1974) 988-989
22. Dinizo S.E., Freerksen R.W., Papst W.E., and Watt D.S. J. Am. Chem. Soc. 99 (1977) 182-186
23. Gross H., and Costisella B. Tetrahedron 38 (1982) 139-145
24. Takahashi K., Shibasaki K., Ogura K., and Iida H. J. Org. Chem. 48 (1983) 3566-3569
25. Takahashi K., Msuda T., Ogura K., and Iida H. Synthesis (1983) 1043-1045
26. Hiyama T., Inoue M., and Saito K. Synthesis (1986) 645-647
27. Katritzky A.R., Dorin T., and Linghong X. Synthesis (1996) 1425-1427
28. Satoh T., Nakamura A., Iriuchijima A., Hayashi Y., and Kubota K. Tetrahedron 57 (2001) 9689-9696
29. Huh D.K., Jeong J.S., Lee H.B., Ryu H., and Kim G. Tetrahedron 58 (2002) 9925-9932
30. Zhou G.B., Zhang P.F., and Pan Y.J. Tetrahedron 61 (2005) 5671-5677
31. McNulty J., Das P., and Gosciniak D. Tetrahedron Lett. 49 (2008) 281-285
32. Cafiero L.R., and Snowden T.S. Org. Lett. 10 (2008) 3853-3856
33. This reagent is available from the Aldrich Chemical Company.
34. Degenhardt C.R. Synth. Commun. 12 (1982) 415-421
35. Dufrechou S., Combret J.C., Malhiac C., and Collignon N. Phosphorus Sulfur Silicon Relat. Elem. 127 (1997) 1-14
36. van Staden L.F., Gravestock D., and Ager D.J. Chem. Soc. Rev. 31 (2002) 195-200
37. Padwa A., Eisenbarth P., Venkataramana M.K., and Wong G.S.K. J. Org. Chem. 52 (1987) 2427-2432
38. Zumstein, F; Klingseisen, F. Ger. Offen DE 4029444 A1, 1990.
39. Zhou G.B., Zhang P.F., and Pan Y.J. Tetrahedron 61 (2005) 5671-5677
40. Adamczyk M., and Watt D.S. J. Org. Chem. 49 (1984) 4226-4237
41. Milne J.E., Murry J.A., King A., and Larsen R.D. J. Org. Chem. 74 (2009) 445-447
42. Ando A., Miki T., and Kumadaki I. J. Org. Chem. 53 (1988) 3637-3639
43. Moreira D.R.M., Lima-Leite A.C., Pinheiro-Ferreira P.M., da Costa P.M., Costa-Lotufo L.V., de Moraes M.O., Brondani D.J., and Pessoca C.O. Eur. J. Med. Chem. 42 (2007) 351-357
44. Li P., and Alper H. J. Org. Chem. 51 (1986) 4354-4356
45. Niu D.F., Xiao N.L.P., Zhang A.J., Zhang G.R., Tan Q.Y., and Lu J.X. Tetrahedron 64 (2008) 10517-10520
46. Chakravarti S., and Swaminathan M. Indian J. Chem. 11 (1934) 107-113