Synthesis of 4-functionalized indoles via benzyne cyclization of N-(2-lithioallyl)-2-fluoroanilines

Authors
Barluenga, J Fananas, FJ Sanz, R Fernandez, Y
Citation
J. Barluenga et al., Synthesis of 4-functionalized indoles via benzyne cyclization of N-(2-lithioallyl)-2-fluoroanilines, TETRAHEDR L, 40(5), 1999, pp. 1049-1052
Citations number
20
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
5
Year of publication
1999
Pages
1049 - 1052
Database
ISI
SICI code
0040-4039(19990129)40:5<1049:SO4IVB>2.0.ZU;2-L
Abstract
Treatment of N-(2-bromoallyl)-N-methyl-2-fluoroaniline with tert-butyllithi um affords 1,3-dimethyl-4-lithioindole, via intramolecular addition to a te thered benzyne intermediate. Further reaction with electrophiles leads to 4 -functionalized 3-methylindoles. (C) 1999 Elsevier Science Ltd. All rights reserved.