RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2010(15): 2571-2576
DOI: 10.1055/s-0029-1218824
DOI: 10.1055/s-0029-1218824
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Three-Component One-Pot Synthesis of 3-(2-Furanyl)indoles from Acetylenedicarboxylate, Isocyanide, and 3-Formylindole
Weitere Informationen
Received
29 March 2010
Publikationsdatum:
18. Juni 2010 (online)
Publikationsverlauf
Publikationsdatum:
18. Juni 2010 (online)
Abstract
The zwitterions derived from isocyanide and dimethyl acetylenedicarboxylate undergo smooth condensation with 3-formylindoles in benzene at room temperature to give the corresponding 3-(2-furanyl)indoles in good yields. This method provides a simple and convenient route to produce a wide range of 3-heteroarylindoles in a one-pot operation.
Key words
3-formylindoles - isocyanides - DMAD - zwitterions - 3-furanylindoles
-
1a
Armstrong RW.Combs AP.Tempest PA.Brown SD.Keating TA. Acc. Chem. Res. 1996, 29: 123 -
1b
Terret NK.Gardner M.Gordon DW.Kobylecki RJ.Steel J. Tetrahedron 1995, 51: 8135 - 2
Zhu J.Bienaymé H. Multicomponent Reactions Wiley-VCH; Weinheim: 2005. -
3a
Nair V.Vinod AU.Rajesh C. J. Org. Chem. 2001, 66: 4427 -
3b
Nair V.Sindu M.Varma LR. J. Org. Chem. 2004, 69: 1413 -
3c
Nair V.Bindu S.Sreekumar V.Rath NP. Org. Lett. 2003, 5: 665 -
3d
Nair V.Bijju AT.Vinod AU.Suresh E. Org. Lett. 2005, 7: 5139 -
3e
Nair V.Bindu S.Balagopal L. Tetrahedron Lett. 2001, 42: 2043 -
3f
Nair V.Sheela KC.Radhakrishnan KV.Rath NP. Tetrahedron Lett. 1998, 39: 5627 -
4a
Nair V.Bijju AT.Abhilash KG.Menon RS.Suresh E. Org. Lett. 2005, 11: 2121 -
4b
Nair V.Sreekumar V.Bindu S.Suresh E. Org. Lett. 2005, 7: 2297 -
4c
Nair V.Deepthi A.Poonooth M.Santhamma B.Vellantha S.Babu BP.Mohan R.Suresh E. J. Org. Chem. 2006, 71: 2313 -
4d
Nair V.Vellantha S.Poonooth M.Mohan R.Suresh E. Org. Lett. 2006, 8: 507 -
4e
Nair V.Santhamma B.Sreekumar V.Chiaroni A. Org. Lett. 2002, 4: 282 -
4f
Nair V.Vinod AU. Chem. Commun. 2000, 1019 -
4g
Shaabani A.Rezayan AH.Ghasemi S.Sarvary A. Tetrahedran Lett. 2009, 50: 1456 -
5a
Shaabani A.Soleimani E.Rezayan AH.Sarvary A.Khavasi HR. Org. Lett. 2008, 10: 2581 -
5b
Nair V.Bindu S.Dhanya R.Rajesh C.Bhadbhade MM.Manoj K. Org. Lett. 2004, 6: 4743 -
5c
Shaabani A.Maleki A.Rad JM. J. Org. Chem. 2007, 72: 6309 -
6a
Shaabani A.Ghadari R.Sarvay A.Rezayan AH. J. Org. Chem. 2009, 74: 4372 -
6b
Waldmann H.Kedhar V.Duckert H.Schurmann M.Oppel I.Kumar K. Angew. Chem. Int. Ed. 2008, 47: 6869 -
6c
Shaabani A.Rezayan AH.Sarvary A.Khavasi HR. Tetrahedran Lett. 2008, 49: 1469 -
6d
Nair V.Nair JS.Vinod AU.Rath NP. J. Chem. Soc., Perkin Trans. 1 1997, 3129 -
7a
Indoles
Sundberg RJ. Academic Press; San Diego: 1996. -
7b
Gribble GW. J. Chem. Soc., Perkin Trans. 1 2000, 1045 -
7c
Cacchi S.Fabrizi G. Chem. Rev. 2005, 105: 2873 -
7d
Humphrey GR.Kuethe JT. Chem. Rev. 2006, 106: 2875 -
8a
Bandini M.Melloni A.Umani-Ronchi A. Angew. Chem. Int. Ed. 2004, 43: 550 -
8b
Austin JF.MacMillan DWC. J. Am. Chem. Soc. 2002, 124: 1172 -
8c
Jensen KB.Thorhange J.Hazel RG.Jorgensen KA. Angew. Chem. Int. Ed. 2001, 40: 160 -
9a
Campbell MM.Cosford N.Zongli L.Sainsbury M. Tetrahedron 1987, 43: 1117 -
9b
Sun C.Ji S.-J.Liu Y. Tetrahedran Lett. 2007, 48: 8987 - 10
Robinson B. Chem. Rev. 1963, 63: 373 -
11a
Nair V.Sreekanth AR.Abhilash N.Bhadbhade MM.Gannade RC. Org. Lett. 2002, 4: 3577 -
11b
Yadav JS.Reddy BVS.Yadav NN.Gupta MK. Tetrahedron Lett. 2008, 49: 2815 - 12
Yadav JS.Reddy BVS.Yadav NN.Gupta MK.Sridhar BS. J. Org. Chem. 2008, 73: 6857