A direct entry to the 1-methoxyindole skeleton and to the corresponding indoles by a novel rearrangement: General syntheses of substituted 1-methoxyindoles

Tetrahedron Letters

Volumn 44, Issue 37, 2003, Pages 7065-7069

  Selvakumar, N ^a   Reddy, B Yadi ^a   Azhagan, A Malar ^a   Khera, Manoj Kumar ^a   Babu, J Moses ^a   Iqbal, Javed ^a  

^a DR REDDY'S LABORATORIES LTD   (India)

Author keywords

Alkaloid; Alkylation; Decarboxylation; Nucleophilic catalysis; Rearrangement

Indexed keywords

1 METHOXYINDOLE; INDOLE DERIVATIVE; NITRO DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; METHODOLOGY; REACTION ANALYSIS; SYNTHESIS;

EID: 0041742189     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01744-1     Document Type: Article

References (20)

1. Somei M. Heterocycles. 50:1999;1157.
2. Acheson R.M. Katritzky A.R. Advances in Heterocyclic Chemistry. 51:1990;105-175 Academic Press, San Diego.
3. Ito C., Wu T.-S., Furukawa H. Chem. Pharm. Bull. 36:1988;2377.
4. Ohmoto T., Koike K. Chem. Pharm. Bull. 31:1983;3198.
5. Sung Y.-I., Koike K., Nikaido T., Ohmoto T., Sankawa U. Chem. Pharm. Bull. 32:1984;1872.
6. Konda Y., Onda M., Hirano A., Omura S. Chem. Pharm. Bull. 28:1980;2987.
7. Gribble, G. W. ibid 1996; pp. 207-257. Sundberg R.J. Katritzky K.R., Rees C.W., Scriven E.F.V., Bird C.W. Comprehensive Heterocyclic Chemistry II. 2:1996;119-206 Pergamon, Oxford, Gribble, G. W. ibid 1996; pp. 207-257.
8. Gribble, G. W. ibid 1996; pp. 207-257. Sundberg R.J. Katritzky K.R., Rees C.W., Scriven E.F.V., Bird C.W. Comprehensive Heterocyclic Chemistry II. 2:1996;119-206 Pergamon, Oxford, Gribble, G. W. ibid 1996; pp. 207-257.
9. Acheson R.M., Hunt P.G., Littlewood D.M., Murrer B.A., Rosenberg H.E. J. Chem. Soc., Perkin Trans. 1. 1978;1117.
10. Somei M., Shoda T. Heterocycles. 16:1981;1523.
11. Somei M., Kawasaki T. Heterocycles. 29:1989;1251.
12. Selvakumar N., Yadi Reddy B., Sunil Kumar G., Iqbal J. Tetrahedron Lett. 42:2001;8395.
13. 3: C, 72.57; H, 5.38; N, 4.98; found: C, 72.37; H, 5.16; N, 5.25.
14. Stauss U., Harter H.P., Neuenschwander M., Schindler O. Helv. Chim. Acta. 55:1972;771.
15. ++1), 220.
16. ++1), 220.
17. Kraphcho A.P., Lovey A.J. Tetrahedron Lett. 14:1973;957.
18. Compound 27 was prepared as follows. Also see: Selvakumar, N.; Azhagan, M. A.; Srinivas, D.; Krishna, G. G. Tetrahedron Lett. 2002, 43, 9175.
19. ++1), 254.
20. Selvakumar N., Khera M.K., Reddy B.Y., Srinivas D., Azhagan M.A., Iqbal J. Tetrahedron Lett. 44:2003;7071.