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Synlett 2002(9): 1514-1516
DOI: 10.1055/s-2002-33528
DOI: 10.1055/s-2002-33528
LETTER
© Georg Thieme Verlag Stuttgart · New York
Novel Synthetic Method for
2,3-Dihydro-3-halo-3-methylindole from
N-Acetyl-2-isopropenylaniline
by Intramolecular Haloamination
Further Information
Received
4 June 2002
Publication Date:
17 September 2002 (online)
Publication History
Publication Date:
17 September 2002 (online)

Abstract
We describe a novel, practical method for synthesis of 2,3-dihydro-3-haloindole from an o-aminostyrene derivative via haloamination, in which the protective group on the nitrogen and α-alkyl substituents on styrene are critical.
Key words
2,3-dihydro-3-haloindole - haloamination - o-aminostyrene - NBS - NCS
-
1a
Sundberg RJ. Indoles Academic Press; London: 1996. -
1b
Li JJ. In Alkaloids: Chemical and Biological Perspectives Vol. 14:Pelletier SW. Wiley; New York: 1999. p.437 - 2
Yamanaka M.Arisawa M.Nishida A.Nakagawa M. Tetrahedron Lett. 2002, 43: 2403 - 3
Yamanaka M.Nishida A.Nakagawa M. Org. Lett. 2000, 2: 159 - 4
Dudley KH.Miller HW. Tetrahedron Lett. 1968, 5: 571 -
5a
Yamaguchi M.Arisawa M.Hirama M. Chem. Commun. 1998, 1399 -
5b
Larock RC.Hightower TR.Hasvold LA.Peterson KP. J. Org. Chem. 1996, 61: 3584 -
5c
Kasahara A.Izumi T.Yanai H.Murakami S.Yusa A.Kon H.Kikuchi T.Tsuda S.Kubo N.Takatori M.Nikaido T. Bulletin Yamagata University 1986, 19: 39 -
5d
Hegedus LS.Allen GF.Bozell JJ.Waterman EL. J. Am. Chem. Soc. 1978, 100: 5800 - 6
Danishefsky S.Berman EM.Ciufolini M.Etheredge SJ.Segnuller BE. J. Am. Chem. Soc. 1985, 107: 3891 - 7
Cenini S.Console S.Crotti C.Tollari S. J. Organomet. Chem. 1993, 451: 157