Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2005(15): 2400-2402
DOI: 10.1055/s-2005-872680
DOI: 10.1055/s-2005-872680
LETTER
© Georg Thieme Verlag Stuttgart · New York
Regioselective Halogenation of 6-Azaindoles: Efficient Synthesis of 3-Halo-2,3-disubstituted-6-azaindole Derivatives
Further Information
Received
2 June 2005
Publication Date:
07 September 2005 (online)
Publication History
Publication Date:
07 September 2005 (online)
![](https://www.thieme-connect.de/media/synlett/200515/lookinside/thumbnails/10.1055-s-2005-872680-1.jpg)
Abstract
A mild and efficient synthesis of 3-halo-2-substituted-6-azaindoles was developed by regioselective halogenation of 6-azaindole systems. The transformation was achieved with copper(II) bromide in acetonitrile at room temperature.
Key words
regioselective halogenation of 6-azaindoles - pyrrolopyridine - copper (II) bromide
-
1a
Maignan S.Guilloteau J.-P.Choi-Sledeki YM.Becker MR.Ewing WR.Pauls HW.Spada AP.Mikol V. J. Med. Chem. 2003, 46: 685 -
1b
Choi-Sledeski YM.Kearney R.Poli G.Pauls H.Gardner C.Gong Y.Becker M.Davis R.Spada A.Liang G.Chu V.Brown K.Collussi D.Leadley R.Rebello S.Moxey P.Morgan S.Bentley R.Kasiewski C.Maignan S.Guilloteau J.-P.Mikol V. J. Med. Chem. 2003, 46: 681 -
1c
Marminon C.Pierre A.Pfeiffer B.Perez VS.Joubert A.Bailly C.Renard P.Hickman J.Prudhomme M. J. Med. Chem. 2003, 46: 609 -
1d
Kuo G.-H.Prouty C.DeAngelis A.Shen L.O’Neil DJ.Shah C.Connolly PJ.Murray WV.Conway BR.Cheung P.Westover L.Xu JZ.Look RA.Demarest KT.Emanuel S.Middleton SA.Jolloffe L. J. Med. Chem. 2003, 46: 4021 -
1e
Kulagowski JJ, andLeeson PD. inventors; US 5563152. -
1f
DiNinno FP,Guthikonda RN, andMeurer LC. inventors; US 5532261. -
1g
Hunsch W,Angerbauer R,Fey P,Bisschoff H,Bender J, andSchmidt D. inventors; US 5120782. -
1h
Patchett AA,Mantlo NB, andGreenlee WJ. inventors; US 5124335. -
1i
Scherlock MH, andTom WC. inventors; US 5023265. -
1j
Anderson PL. inventors; US 4751235. -
1k
Fisher MH.Schwartzkopf G.Hoff DR. J. Med. Chem. 1972, 15: 1168 -
2a
Gribble GW. J. Chem. Soc., Perkin Trans. 1 2000, 1045 ; and references therein -
2b
Gribble GW. Contemp. Org. Synth. 1994, 1: 145 ; and references therein -
3a
Greenhill JV. In Comprehensive Heterocyclic Chemistry Vol. 4:Katritzky AR.Rees CW.Bird CW.Cheeseman GWH. Pergamon; Oxford: 1984. p.497 -
3b
Yakhontov LN.Prokopov AA. Russ. Chem. Rev. 1980, 49: 428 -
3c
Yakhontov LN. Russ. Chem. Rev. 1968, 37: 551 -
3d
Wilette RE. Adv. Heterocycl. Chem. 1968, 9: 27 -
3e
Le Hyaric M.Almeida MV.Souza MVN. Quim. Nova 2002, 25: 1165 - 4
Xu L.Lewis IR.Davidsen SK.Summers JB. Tetrahedron Lett. 1998, 39: 5159 -
5a
Ujjainwalla F.Warner D. Tetrahedron Lett. 1998, 39: 5355 -
5b
Park SS.Choi J.-K.Yum EK.Ha D.-C. Tetrahedron Lett. 1998, 39: 627 - 6
Hands D.Bishop B.Cameron M.Edwards JS.Cottrell IF.Wright SHB. Synthesis 1996, 877 - 7
Estel L.Marsais F.Queguiner G. J. Org. Chem. 1988, 53: 2740 - 8
Kuzmich D.Mulrooney C. Synthesis 2003, 1671 -
9a
Turner JA. J. Org. Chem. 1983, 48: 3401 -
9b
See ref. 1k.
-
9c
Cadgan JIG.Cameron-Wood M.Mackie RK.Searle RJG. J. Chem. Soc. 1965, 4831 -
9d
Davis ML.Wakefield BJ.Wardell JA. Tetrahedron 1992, 48: 939 -
9e
Kumar V.Dority JA.Bacon ER.Singh B.Lesher GY. J. Org. Chem. 1992, 57: 6995 - 10
Dormoy JR.Heymes A. Tetrahedron 1993, 49: 2885 -
11a
Song JJ.Tan Z.Gallou F.Xu J.Yee NK.Senanayake CH. J. Org. Chem. 2005, 70: 6512 -
11b
Harcken C.Ward Y.Thomson D.Riether D. Synlett in press -
12a
Prokopov AA.Yakhontov LN. Khim. Geterotsikl. Soedin. 1978, 496 -
12b
Yakhontov LN.Azimov VA.Lapan EI. Tetrahedron Lett. 1969, 10: 1909 - 13
Alvarez M.Fernandez D.Joule JA. Synthesis 1999, 615 - 14
Minakata S.Komatsu M.Ohshiro Y. Synthesis 1992, 661 - 15
Zhang Z.Yang Z.Wong H.Zhu J.Meanwell NA.Kadow JF.Wang T. J. Org. Chem. 2002, 67: 6226 -
16a
Herz W.Tocker S. J. Am. Chem. Soc. 1955, 77: 6355 -
16b
Cox ED.Cook JM. Chem. Rev. 1995, 95: 1797 -
16c
Klutchko S.Hodges JC.Blankley CJ.Colbry NL. J. Heterocycl. Chem. 1991, 28: 97 -
16d
Sanchez-Sanchez MM.Tel-Alberdi LM.Rioseras MJ.Rico-Ferreira MR.Bermejo-Gonzalez F. Bull. Chem. Soc. Jpn. 1993, 66: 91 -
16e
Rousseau J.-F.Dodd RH. J. Org. Chem. 1998, 63: 2731 -
16f
Braestrup C.Nielsen M.Olsen CE. Proc. Natl. Acad. Sci. U.S.A. 1980, 77: 2288 -
16g
De Carvalho PL.Grecksch G.Chapoutier G.Rossier J. Nature 1983, 301: 64 -
16h
Belzung C.Misslim R.Vogel E.Dodd RH.Chapoutier G. Pharmacol., Biochem. Behav. 1987, 28: 29 -
16i
De Carvalho PL.Grecksch G.Cavalheiro EA.Dodd RH.Chapoutier G.Rossier J. Eur. J. Pharmacol. 1984, 103: 287 -
16j
Oakley NR.Jones BJ. Eur. J. Pharmacol. 1980, 68: 381 -
16k
Dodd RH.Doisy X.Potier P.Potier M.-C.Rossier J. Heterocycles 1989, 28: 1101 -
16l
Dekhane M.Potier P.Dodd RH. Tetrahedron 1993, 49: 8139 -
16m
Dekhane M.Dodd RH. Tetrahedron 1994, 50: 6299 -
16n
Thomet U.Furtmuller R.Sieghart W.Le Hyaric M.Rousseau J.-F.Dodd RH.Venault P.Chapoutier G.Sigel E. Neurosci. Lett. 1999, 269: 63 -
18a
Anderson HJ.Lee S.-F. Can. J. Chem. 1965, 43: 409 -
18b
Cordell GA. J. Org. Chem. 1975, 40: 3161 -
18c
Petruso S.Caronna S.Sprio V. J. Heterocycl. Chem. 1990, 27: 1209
References
Various mixtures of mono-brominated species at C-3 and on the furan ring were observed in our hands.