N-alkylation of indole compounds in modified Wittig-Horner reaction

Synthetic Communications

Volumn 37, Issue 9, 2007, Pages 1491-1494

  Singh, Anil K ^a   Asefa, Abera ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

Author keywords

3 styrylindole; N alkylation; Wittig Horner reaction

Indexed keywords

INDOLE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; COLUMN CHROMATOGRAPHY; HORNER REACTION; HORNER WADSWORTH EMMONS REACTION; OLEFINATION; ROOM TEMPERATURE; TEMPERATURE MEASUREMENT;

EID: 34248585883     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701229073     Document Type: Article

References (10)

1. Santaniello, E.; Farachi, C.; Pointi, F. N-Alkylation of pyrrol and indole catalyzed by crown ethers. Synthesis 1979, 617-618.
2. Rubottom, G. M.; Chabala, J. C. The alkylation of indole sodium salt. Synthesis 1972, 566.
3. Kunieda, T.; Witkop, B. Selective N-methylations of heterocycles with dimethyloxosulfonium methylide. J. Org. Chem. 1970, 35, 3981-3982.
4. Reinecke, M. G.; Sebastian, J. F.; Johnson, H. W.; Pyun, C. The effect of solvent and cation on the reaction of organometallic derivatives of indole with methyl iodide. J. Org. Chem. 1972, 37, 3066-3068.
5. Barco, A.; Benetti, S.; Pollini, G. P. The use of phase-transfer catalysis for the N- alkylation of indole. Synthesis 1976, 124-125.
6. Bocchi, V.; Casnati, G.; Dossena, A.; Villani, F. Synthesis of N-alkylindoles using tetraalkylammoniumsalt catalysis. Synthesis 1976, 414-416.
7. Singh, A. K.; Manjula, D. Bacteriorhodopsin analogs from diphenylpolyene chromophores. Photochem. Photobiol. 2003, 78, 503-510.
8. Kosolapoff, G. M. The synthesis of phosphonic and phosphinic acids. Org. React. 1951, 6, 273-338.
9. Davis, R.; Abraham, S.; Rath, N. P.; Das, S. Observation of a non-conventional Horner-Wadsworth-Emmons olefination product and the effect of the lateral ethyl substitution on the solid state fluorescence. New J. Chem. 2004, 28, 1368-1372.
10. Hulvat, J. F.; Sofo, M.; Tajima, K.; Stupp, S. I. Self-assembly and luminescence of oligo(p-phenylene) amphiphiles. J. Am. Chem. Soc. 2005, 127, 366-372.