Three-Component One-Pot Synthesis
of 3-(2-Furanyl)indoles from Acetylenedicarboxylate, Isocyanide,
and 3-Formylindole

B. V. Subba Reddy; A. Mallikarjun Reddy; D. Somashekar; J. S. Yadav; B. Sridhar

doi:10.1055/s-0029-1218824

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Synthesis 2010(15): 2571-2576
DOI: 10.1055/s-0029-1218824

PAPER

Three-Component One-Pot Synthesis of 3-(2-Furanyl)indoles from Acetylenedicarboxylate, Isocyanide, and 3-Formylindole

B. V. Subba Reddy*^a, A. Mallikarjun Reddy^a, D. Somashekar^a, J. S. Yadav^a, B. Sridhar^b
^a Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007, India
^b Centre for X-ray Crystallography, Indian Institute of Chemical Technology, Hyderabad 500 007, India
e-Mail: basireddy@iict.res.in;

Further Information

Publication History

Received 29 March 2010
Publication Date:
18 June 2010 (online)

Abstract
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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

References

1a Armstrong RW. Combs AP. Tempest PA. Brown SD. Keating TA. Acc. Chem. Res. 1996, 29: 123

Google Scholar
1b Terret NK. Gardner M. Gordon DW. Kobylecki RJ. Steel J. Tetrahedron 1995, 51: 8135

Google Scholar
2 Zhu J. Bienaymé H. Multicomponent Reactions Wiley-VCH; Weinheim: 2005.

Google Scholar
3a Nair V. Vinod AU. Rajesh C. J. Org. Chem. 2001, 66: 4427

Google Scholar
3b Nair V. Sindu M. Varma LR. J. Org. Chem. 2004, 69: 1413

Google Scholar
3c Nair V. Bindu S. Sreekumar V. Rath NP. Org. Lett. 2003, 5: 665

Google Scholar
3d Nair V. Bijju AT. Vinod AU. Suresh E. Org. Lett. 2005, 7: 5139

Google Scholar
3e Nair V. Bindu S. Balagopal L. Tetrahedron Lett. 2001, 42: 2043

Google Scholar
3f Nair V. Sheela KC. Radhakrishnan KV. Rath NP. Tetrahedron Lett. 1998, 39: 5627

Google Scholar
4a Nair V. Bijju AT. Abhilash KG. Menon RS. Suresh E. Org. Lett. 2005, 11: 2121

Google Scholar
4b Nair V. Sreekumar V. Bindu S. Suresh E. Org. Lett. 2005, 7: 2297

Google Scholar
4c Nair V. Deepthi A. Poonooth M. Santhamma B. Vellantha S. Babu BP. Mohan R. Suresh E. J. Org. Chem. 2006, 71: 2313

Google Scholar
4d Nair V. Vellantha S. Poonooth M. Mohan R. Suresh E. Org. Lett. 2006, 8: 507

Google Scholar
4e Nair V. Santhamma B. Sreekumar V. Chiaroni A. Org. Lett. 2002, 4: 282

Google Scholar
4f Nair V. Vinod AU. Chem. Commun. 2000, 1019

Google Scholar
4g Shaabani A. Rezayan AH. Ghasemi S. Sarvary A. Tetrahedran Lett. 2009, 50: 1456

Google Scholar
5a Shaabani A. Soleimani E. Rezayan AH. Sarvary A. Khavasi HR. Org. Lett. 2008, 10: 2581

Google Scholar
5b Nair V. Bindu S. Dhanya R. Rajesh C. Bhadbhade MM. Manoj K. Org. Lett. 2004, 6: 4743

Google Scholar
5c Shaabani A. Maleki A. Rad JM. J. Org. Chem. 2007, 72: 6309

Google Scholar
6a Shaabani A. Ghadari R. Sarvay A. Rezayan AH. J. Org. Chem. 2009, 74: 4372

Google Scholar
6b Waldmann H. Kedhar V. Duckert H. Schurmann M. Oppel I. Kumar K. Angew. Chem. Int. Ed. 2008, 47: 6869

Google Scholar
6c Shaabani A. Rezayan AH. Sarvary A. Khavasi HR. Tetrahedran Lett. 2008, 49: 1469

Google Scholar
6d Nair V. Nair JS. Vinod AU. Rath NP. J. Chem. Soc., Perkin Trans. 1 1997, 3129

Google Scholar
7a Indoles Sundberg RJ. Academic Press; San Diego: 1996.

Google Scholar
7b Gribble GW. J. Chem. Soc., Perkin Trans. 1 2000, 1045

Google Scholar
7c Cacchi S. Fabrizi G. Chem. Rev. 2005, 105: 2873

Google Scholar
7d Humphrey GR. Kuethe JT. Chem. Rev. 2006, 106: 2875

Google Scholar
8a Bandini M. Melloni A. Umani-Ronchi A. Angew. Chem. Int. Ed. 2004, 43: 550

Google Scholar
8b Austin JF. MacMillan DWC. J. Am. Chem. Soc. 2002, 124: 1172

Google Scholar
8c Jensen KB. Thorhange J. Hazel RG. Jorgensen KA. Angew. Chem. Int. Ed. 2001, 40: 160

Google Scholar
9a Campbell MM. Cosford N. Zongli L. Sainsbury M. Tetrahedron 1987, 43: 1117

Google Scholar
9b Sun C. Ji S.-J. Liu Y. Tetrahedran Lett. 2007, 48: 8987

Google Scholar
10 Robinson B. Chem. Rev. 1963, 63: 373

Crossref Google Scholar
11a Nair V. Sreekanth AR. Abhilash N. Bhadbhade MM. Gannade RC. Org. Lett. 2002, 4: 3577

Google Scholar
11b Yadav JS. Reddy BVS. Yadav NN. Gupta MK. Tetrahedron Lett. 2008, 49: 2815

Google Scholar
12 Yadav JS. Reddy BVS. Yadav NN. Gupta MK. Sridhar BS. J. Org. Chem. 2008, 73: 6857

Crossref PubMed Google Scholar