A mild and efficient CAN mediated oxidation of Morita-Baylis-Hillman adducts of 5-methyl-N-alkylisatin to 5-formyl-N-alkylisatin

Tetrahedron Letters

Volumn 49, Issue 13, 2008, Pages 2119-2123

  Shanmugam, Ponnusamy ^a   Vaithiyanathan, Vadivel ^a   Selvakumar, Kodirajan ^a  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

Author keywords

Aromatic aldehydes; Aryl methyl oxidation; CAN; Isatin; Morita Baylis Hillman adduct

Indexed keywords

2 (1 ETHYL 5 FORMYL 3 HYDROXY 2 OXOINDOLIN 3 YL)ACRYLONITRILE; 2 (5 FORMYL 3 HYDROXY 1 METHYL 2 OXOINDOLIN 3 YL)ACRYLONITRILE; 5 METHYL N ALKYLISATIN DERIVATIVE; ACRYLONITRILE; AMMONIUM NITRATE; CERIUM; METHYL 2 (1 ETHYL 5 FORMYL 3 HYDROXY 2 OXOINDOLIN 3 YL) ACRYLATE; METHYL 2 (5 FORMYL 3 HYDROXY 1 METHYL 2 OXOINDOLIN 3 YL) ACRYLATE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL REACTION; OXIDATION; SYNTHESIS;

EID: 39649089131     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.01.119     Document Type: Article

References (46)

1. Brühne F., and Wright E. Industrial Organic Chemicals: Starting Materials and Intermediates-Ullmann's Encyclopedia Vol. 2 (1999), Wiley-VCH, Weinheim 673-692 and references cited therein
2. Fritz-Langhals E., and Kunath B. Tetrahedron Lett. 39 (1998) 5955-5956
3. Potthast A., Rosenaq T., Chen C.-L., and Gratzl J.S. J. Org. Chem. 60 (1995) 4320-4321
4. Lieberman S.V., and Connor R. Org. Synth. 18 (1938) 61
5. Nishimura T. Org. Synth. 36 (1956) 58
6. Hartford W.H., and Darrin M. Chem. Rev. 58 (1958) 1-61
7. Vlattas I., Harrison I.T., Tokes L., Fried J.H., and Cross A.D. J. Org. Chem. 33 (1968) 4176-4179
8. Marvel C.S., Saunders J.S., and Overberger C.G. J. Am. Chem. Soc. 68 (1946) 1085-1088
9. Carpenter M.S., Easter W.M., and Wood T.F. J. Org. Chem. 16 (1951) 586-617
10. Syper L. Tetrahedron Lett. 7 (1966) 4493-4498
11. Trahanovsky W.S., and Young L.B. J. Org. Chem. 31 (1966) 2033-2035
12. Gilman H., Brannen C.G., and Ingham R.K. J. Am. Chem. Soc. 78 (1956) 1689-1692
13. Ganin E., and Amer I. Synth. Commun. 25 (1995) 3149-3154
14. Hosseinzadeh R., Tajbakhsh M., and Vahedi H. Synlett (2005) 2769-2770
15. Ghaffarzadeh M., Bolourtchian M., Gholamhosseni M., and Mohsenzadeh F. Appl. Catal. A: Gen. 333 (2007) 131-135
16. Nair V., and Deepthi A. Chem. Rev. 107 (2007) 1861-1891
17. Nair V., Balagopal L., Rajan R., and Mathew J. Acc. Chem. Res. 37 (2004) 21-30 and references cited therein
18. Thyrann T., and Lightner D.A. Tetrahedron Lett. 36 (1995) 4345-4348
19. Trahanovsky W.S., and Young L.B. J. Chem. Soc. (1965) 5777
20. Trahanovsky W.S., and Young L.B. J. Org. Chem. 32 (1967) 3865
21. Dallacort A.D., Barbera A.L., and Mandolini L. J. Chem. Res. (S) (1983) 44
22. Hatanaka Y., Imamoto T., and Yokoyama M. Tetrahedron Lett. 24 (1983) 2399
23. Omote Y., and Tomotake A. J. Chem. Res. (S) (1987) 10
24. da Silva J.F.M., Garden S.J., and Pinto A.C. J. Braz. Chem. Soc. 12 (2001) 273-324
25. Saxton J.E. The Monoterpenoid Indole Alkaloids (1983), Wiley, New York
26. Cordell G.A. The Alkaloids: Chemistry and Biology Vol. 5 (1998), Academic, San Diego
27. Cui C.-B., Kakeya H., and Osada H. Tetrahedron 52 (1996) 12651-12666
28. Xue J., Zhang Y., Wang X.-I., Fun H.K., and Xu J.-H. Org. Lett. 2 (2000) 2583-2586
29. Klumpp D.A., Yeung K.Y., Prakash G.K.S., and Olah G.A. J. Org. Chem. 63 (1998) 4481-4484
30. Basavaiah D., Rao A.J., and Satyanarayana T. Chem. Rev. 103 (2003) 811-891
31. Derewes S.E., and Roos G.H.P. Tetrahedron 44 (1988) 4653-5670
32. Lee K.Y., Gowrisankar S., and Kim J.N. Bull. Korean Chem. Soc. 26 (2005) 1481-1490
33. Shanmugam P., Vaithiyanathan V., and Baby V. Tetrahedron 62 (2006) 4342-4347
34. Shanmugam P., Vaithiyanathan V., and Baby V. Tetrahedron Lett. 47 (2006) 6851-6855
35. Shanmugam P., Vaithiyanathan V., and Baby V. Aust. J. Chem. 60 (2007) 296-301
36. Shanmugam P., Baby V., and Vaithiyanathan V. Aust. J. Chem. 60 (2007) 850-856
37. Shanmugam P., Baby V., and Suchithra M. Org. Lett. 9 (2007) 4095
38. Shanmugam P., Vaithiyanathan V., Baby V., and Suchithra M. Tetrahedron Lett. 48 (2007) 9190-9194
39. de Klein W.J. In: Mijs W.J., and de Jonge C.R.H.I. (Eds). Organic Syntheses by Oxidation with Metal Compounds (1986), Plenum, New York Chapter 4
40. Riley H.A., and Gray A.R. Org. Synth. Coll. Vol. 2 (1943) 509
41. Zee-Cheng K.-Y., and Cheng C.C. J. Hetrocycl. Chem. 4 (1967) 163
42. Jones A.W., Wahyuninigsih T.D., Pchalek K., Kumar N., and Black D.StC. Tetrahedron 61 (2005) 10490-10500
43. Ahrendt D. Manganese Compounds as Oxidizing Agents in Organic Chemistry (1981), Open Court, La Salle, IL Chapter 5
44. Iliefski T., Li S., and Lundquist K. Tetrahedron Lett. 39 (1998) 2413-2416
45. Lee H., and Harvey R.G. J. Org. Chem. 53 (1988) 4587
46. Fletton R.A., Humber D.C., Roberts S.M., and Wright J.L. J. Chem. Soc., Perkin Trans. 1 (1985) 1523