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-00000084.xml
Synthesis 2008(24): 4036-4040
DOI: 10.1055/s-0028-1083236
DOI: 10.1055/s-0028-1083236
PSP
© Georg Thieme Verlag
Stuttgart ˙ New YorkSynthesis of Indoles via Diethylzinc-Mediated Intramolecular Hydroamination Reactions of Alkynyl Sulfonamides
Further Information
Received
17 April 2008
Publication Date:
01 December 2008 (online)
Publication History
Publication Date:
01 December 2008 (online)

Abstract
A series of indole derivatives were synthesized through the intramolecular hydroamination of alkynyl sulfonamides using 20 mol% of diethylzinc as the catalyst. A tandem cyclization-nucleophilic addition reaction was also possible to afford C2,C3-disubstituted indoles using 120 mol% of diethylzinc.
Key words
diethylzinc - intramolecular hydroamination - alkynyl sulfonamides - cyclizations - tandem reactions
- 1a
Hibino S.Choshi T. Nat. Prod. Rep. 2002, 19: 148MissingFormLabel - 1b
Gupta RR. Heterocyclic Chemistry Vol. 2: Springer; New York: 1999. p.193MissingFormLabel - 1c
Rahman A.Basha A. Indole Alkaloids Harwood Academic; Amsterdam: 1998.MissingFormLabel - 1d
Dewick PM. Medicinal Natural Products Wiley; Chichester: 1997.MissingFormLabel - 2a
Sundberg RJ. Indoles Academic Press; London: 1996.MissingFormLabel - 2b
Humphery GR.Kuethe JT. Chem. Rev. 2006, 106: 2875MissingFormLabel - 2c
Patil S.Buolamwini JK. Curr. Org. Synth. 2006, 3: 477MissingFormLabel - 2d
Song JJ.Reeves JT.Gallow F.Tan Z.Yee NK. Chem. Soc. Rev. 2007, 36: 1120MissingFormLabel - 3a
Aillaud I.Collin J.Duhayon C.Guillot R.Lyubov D.Schulz E.Trifonov A. Chem. Eur. J. 2008, 14: 2189MissingFormLabel - 3b
Ackermann L.Sandmann R.Villar A.Kaspar LT. Tetrahedron 2007, 64: 769MissingFormLabel - 3c
Ebrahimi D.Kennedy DF.Messerle BA.Hibbert DB. Analyst 2008, 133: 817MissingFormLabel - 4a
Nakamura M.Ilies L.Otsubo S.Nakamura E. Angew. Chem. Int. Ed. 2006, 45: 944MissingFormLabel - 4b
Nakamura M.Ilies L.Otsubo S.Nakamura E. Org. Lett. 2006, 8: 2803MissingFormLabel - 5a
Yin Y.Ma W.-Y.Chai Z.Zhao G. J. Org. Chem. 2007, 72: 5731MissingFormLabel - For related works in this field from our group, see:
- 5b
Yin Y.Zhao G. Heterocycles 2006, 68: 23MissingFormLabel - 5c
Yin Y.Zhao G. J. Fluorine Chem. 2007, 128: 40MissingFormLabel - 6
Gregory YY.Stephenson GA.Mitchell S. Tetrahedron Lett. 2006, 47: 3811 - 7a
Baldwin JE. J. Chem. Soc., Chem. Commun. 1976, 734MissingFormLabel - 7b
Baldwin JE.Cutting J.Dupont W.Kruse L.Sillberman L.Thomas RC. J. Chem. Soc., Chem. Commun. 1976, 736MissingFormLabel - 8a
Yang CX.Patel HH.Ku YY. Synth. Commun. 1997, 27: 2125MissingFormLabel - 8b
Browder CC.Mitchell MO.Smith RL.el-Sulayman G. Tetrahedron Lett. 1993, 34: 6245MissingFormLabel - 8c
Knochel P.Singer RD. Chem. Rev. 1993, 93: 2117 ; and references cited thereinMissingFormLabel - 8d
Bergman J.Venemalm L. Tetrahedron 1990, 46: 6061MissingFormLabel - 9a
Kang Q.Zhao Z.-A.You S.-L. J. Am. Chem. Soc. 2007, 129: 1416MissingFormLabel - 9b
Terada M.Sorimach K. J. Am. Chem. Soc. 2007, 129: 292MissingFormLabel - 9c
Jia Y.-X.Zhong J.Zhu S.-F.Zhang C.-M.Zhou Q.-L. Angew. Chem. Int. Ed. 2007, 46: 5565MissingFormLabel - 9d
Wang YQ.Song J.Hong R.Li HM.Deng L. J. Am. Chem. Soc. 2006, 128: 8186MissingFormLabel - 9e
Trost BM.Quancard J. J. Am. Chem. Soc. 2006, 128: 6314MissingFormLabel - 9f
Li DP.Guo YC.Ding Y.Xiao WJ. Chem. Commun. 2006, 799MissingFormLabel - 9g
Bandini M.Melloni A.Tommasi S.Umani-Ronchi A. Synlett 2005, 1199 ; and references cited thereinMissingFormLabel - 9h
Herrera RP.Sgarzani V.Bernardi L.Ricci A. Angew. Chem. Int. Ed. 2005, 44: 6576MissingFormLabel - 9i
Yasuda M.Somyo T.Baba A. Angew. Chem. Int. Ed. 2005, 44: 1MissingFormLabel