A convenient method of protecting oxindoles

Tetrahedron Letters

Volumn 38, Issue 45, 1997, Pages 7813-7814

  Rajeswaran, Walajapet G ^a,b   Cohen, Louis A ^a  

^a NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

^b MEDICAL COLLEGE OF OHIO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; DICHLOROACETIC ACID; FLUORIDE; INDOLE DERIVATIVE; NITROGEN; TRIETHYLAMINE;

ACETYLATION; ARTICLE; FLUORINATION; SYNTHESIS; TECHNIQUE;

EID: 0030780384     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10090-9     Document Type: Article

References (12)

1. Powers, J.C. Haloindoles and Organometallic Derivatives of Indoles, "Heterocyclic Compounds - Indoles Part II" , Houlihan, W.J. Ed; John Wiley and Sons, Inc. 1972, Chapter 5.
2. a) Phillips, R.S. ; Cohen, L.A. Tetrahedron Lett. 1983, 24, 5555;
3. b) Bergman, J. ; Venemalm, L. J. Org. Chem. 1992, 57, 2495 and references cited therein.
4. a) Bourlot, A.S.; Desarbre, E.; Merour, J.Y. Synthesis 1994, 411;
5. b) Conway, S.C.; Gribble, G.W., Synth. Commun. 1992, 22, 2987.
6. Pallos, F.M.; Brokke, M.E.; Arneklev, D.R. US. Patent 4,021,224 (1977)
7. Hazra, B.G.; Pore, V.S.; Maybhate, S.P., OPPI Briefs 1989, 21, 355 and references cited therein.
8. A typical procedure: To a solution of 1a, b or 3 (2 mmol) in DCE was added dichloroacetyl chloride (2 mmol). The solution was refluxed for 2-4h. Then the solvent was removed and the residue was crystallized from appropriate solvents.
9. 2: C, 49.21; H, 2.89; N, 5.74. Found: C, 49.42; H, 3.00; N, 5.63.
10. 2: C, 51.19; H, 3.51; N, 5.43. Found: C, 51.28; H, 3.56; N, 5.41.
11. 2:C, 52.66; H, 3.09; N, 6.14. Found: C, 52.61; H, 3.14; N, 6.12.
12. 4) and concentrated. The concentrated solution was applied to a preparative TLC plate and eluted with appropriate solvents. Yields : 85-92%