Efficient N-Aroylation of Substituted Indoles with N-Aroylbenzotriazoles

Alan R. Katritzky; Levan Khelashvili; Prabhu P. Mohapatra; Peter J. Steel

doi:10.1055/s-2007-990889

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Synthesis 2007(23): 3673-3677
DOI: 10.1055/s-2007-990889

PAPER

Efficient N-Aroylation of Substituted Indoles with N-Aroylbenzotriazoles

Alan R. Katritzky*^a, Levan Khelashvili^a, Prabhu P. Mohapatra^a, Peter J. Steel^b
^a Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA
^b Chemistry Department, University of Canterbury, Christchurch, New Zealand
Fax: +1(352)3929199; e-Mail: katritzky@chem.ufl.edu;

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Publication History

Received 12 April 2007
Publication Date:
13 November 2007 (online)

Abstract
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Abstract

Stable and easily accessible N-aroylbenzotriazoles react with indoles in the presence of a base to afford the corresponding N-aroylindoles in yields averaging 70%. This method is effective even when both coupling reagents possess electron-donating substituents.

Key words

N-aroylbenzotriazoles - indoles - N-aroylindoles - electron-donating substituents

References

1a Zambre AP. Ganure AL. Shinde DB. Kulkarni VM. J. Chem. Inf. Model. 2007, 47: 635

Crossref Google Scholar
1b Rosenbaum C. Baumhof P. Mazitschek R. Mueller O. Giannis A. Waldmann H. Angew. Chem. Int. Ed. 2004, 43: 224

Crossref Google Scholar
2 Samosorn S. Bremner JB. Ball A. Lewis K. Bioorg. Med. Chem. 2006, 14: 857

Crossref PubMed Google Scholar
3 Cho I.-H, Lim J.-W, Noh J.-Y, Kim J.-H, Park S.-W, Ryu H.-C, Kim J.-H, Chun H.-O, Wang S.-Y, and Lee S.-H. inventors; World Patent WO 031409. ; Chem. Abstr. 2003, 138, 321129
4a Sano H. Noguchi T. Miyajima A. Hashimoto Y. Miyachi H. Bioorg. Med. Chem. Lett. 2006, 16: 3068

Crossref Google Scholar
4b Sano H. Noguchi T. Tanatani A. Hashimoto Y. Miyachi H. Bioorg. Med. Chem. 2005, 13: 3079

Crossref Google Scholar
5 Gross S. Reissig H.-U. Org. Lett. 2003, 5: 4305

Crossref Google Scholar
6a Welstead WJ. Stauffer HF. Sancilio LF. J. Med. Chem. 1974, 17: 544

Article in Thieme Connect Google Scholar
6b Bremner JB. Samosorn S. Ambrus JI. Synthesis 2004, 2653

Article in Thieme Connect Google Scholar
6c Terashima M. Fujioka M. Heterocycles 1982, 19: 91

Article in Thieme Connect Google Scholar
6d Illi VO. Synthesis 1979, 387

Article in Thieme Connect Google Scholar
7a Katritzky AR. Suzuki K. Wang Z. Synlett 2005, 1656

Google Scholar
7b Katritzky AR. Zhang Y. Singh SK. Synthesis 2003, 2795

Google Scholar
7c Katritzky AR. Meher NK. Cai C. Singh SK. Rev. Soc. Quim. Mex. 2004, 48: 275 ; Chem. Abstr. 2005, 143, 26540

Google Scholar
8a Katritzky AR. He H.-Y. Suzuki K. J. Org. Chem. 2000, 65: 8210

Google Scholar
8b Katritzky AR. Yang H. Zhang S. Wang M. ARKIVOC 2002, (xi): 39

Google Scholar
9 Katritzky AR. Hoffmann S. Suzuki K. ARKIVOC 2004, (xii): 14

Google Scholar
10 Katritzky AR. Pastor A. Voronkov MV. J. Heterocycl. Chem. 1999, 36: 777

Crossref Google Scholar
11 Katritzky AR. Suzuki K. Singh SK. He H.-Y. J. Org. Chem. 2003, 68: 5720

Crossref PubMed Google Scholar
12 Zou X. Wang X. Cheng C. Kong L. Mao H. Tetrahedron Lett. 2006, 47: 3767

Crossref Google Scholar
13a Katritzky AR. Pastor A. J. Org. Chem. 2000, 65: 3679

Crossref Google Scholar
13b Katritzky AR. Jiang R. Suzuki K. J. Org. Chem. 2005, 70: 4993

Crossref Google Scholar
14a Katritzky AR. Meher NK. Singh SK. J. Org. Chem. 2005, 70: 7792

Google Scholar
14b Katritzky AR. Abdel-Fattah AAA. Wang M. J. Org. Chem. 2003, 68: 1443

Google Scholar
14c Katritzky AR. Abdel-Fattah AAA. Wang M. J. Org. Chem. 2003, 68; 4932

Google Scholar
15 Katritzky AR. Abdel-Fattah AAA. Akhmedova RG. ARKIVOC 2005, (vi): 329

Google Scholar
16 Katritzky AR. Abdel-Fattah AAA. Gromova AV. Witek R. Steel PJ. J. Org. Chem. 2005, 70: 9211

Crossref Google Scholar
17 Katritzky AR. Suzuki K. Singh SK. Croat. Chem. Acta 2004, 77: 175 ; Chem. Abstr. 2004, 142, 134399

Google Scholar
18 Katritzky AR. Suzuki K. Singh SK. Synthesis 2004, 2645

Article in Thieme Connect Google Scholar
19 Katritzky AR. Angrish P. Hür D. Suzuki K. Synthesis 2005, 397

Article in Thieme Connect Google Scholar
20a Katritzky AR. Angrish P. Suzuki K. Synthesis 2006, 411

Crossref Google Scholar
20b Katritzky AR. Todadze E. Cusido J. Angrish P. Shestopalov AA. Chem. Biol. Drug Des. 2006, 68: 37

Crossref Google Scholar
20c Katritzky AR. Todadze E. Shestopalov AA. Cusido J. Angrish P. Chem. Biol. Drug Des. 2006, 68: 42

Crossref Google Scholar
20d Katritzky AR. Meher G. Angrish P. Chem. Biol. Drug Des. 2006, 68: 326

Crossref Google Scholar
20e Katritzky AR. Tao H. Jiang R. Suzuki K. Kirichenko K. J. Org. Chem. 2007, 72: 407

Crossref Google Scholar
20f Katritzky AR. Cai C. Suzuki K. Singh SK. J. Org. Chem. 2004, 69: 811

Crossref Google Scholar
20g Katritzky AR. Singh SK. Cai C. Bobrov S. J. Org. Chem. 2006, 71: 3364

Crossref Google Scholar
21 Katritzky AR. Yang H. Zhang S. Wang M. ARKIVOC 2002, (xi): 39

Google Scholar
22a Katritzky AR. Rogovoy BV. Kirichenko N. Vvedensky V. Bioorg. Med. Chem. Lett. 2002, 12: 1809

Google Scholar
22b Katritzky AR. Angrish P. Steroids 2006, 71: 660

Google Scholar
22c Katritzky AR. Singh SK. Akhmedova R. Cai C. Bobrov S. ARKIVOC 2007, vi: 6

Google Scholar
23 Katritzky AR. Le KNB. Khelashvili L. Mohapatra PP. J. Org. Chem. 2006, 71: 9861

Crossref Google Scholar
24a Wang X. Zhang Y. Tetrahedron 2003, 59: 4201

Article in Thieme Connect Google Scholar
24b Wang X. Zhang Y. Tetrahedron Lett. 2002, 43: 5431

Article in Thieme Connect Google Scholar
24c Katritzky AR. Angrish P. Synthesis 2006, 4135

Article in Thieme Connect Google Scholar
25 Wang X. Zou X. Li J. Hu Q. Synlett 2005, 3042

Article in Thieme Connect Google Scholar
26a Wang X. Zou X. Du J. J. Chem. Res., Synop. 2006, 64

Article in Thieme Connect Google Scholar
26b Katritzky AR. Shestopalov AA. Suzuki K. Synthesis 2004, 1806

Article in Thieme Connect Google Scholar
27 Singh KN. Kaur A. Synth. Commun. 2005, 35: 2935

Crossref Google Scholar
28 Katritzky AR. Wang M. Zhang S. ARKIVOC 2001, (ix): 19

Google Scholar
29 Katritzky AR. Huang T.-B. Voronkov MV. Steel PJ. J. Org. Chem. 2000, 65: 8069

Crossref Google Scholar

30

Crystal data for 3f: C₁₇H₁₅NO₃, MW 281.30, monoclinic, space group Cc, a = 15.1850 (14), b = 4.3143 (4), c = 21.398 (2) Å, β = 103.703 (3)°, V = 1362.0(2) Å³, F(000) = 592, Z = 4, T = -170 °C, µ (MoKα) = 0.095 mm^-1, D_calcd = 1.372 g.cm^-3, 2θ_max 50° APEX II CCD area detector, MoKα radiation, SHELXS and SHELXL, GOF = 1.08, wR(F²) = 0.074 (all 2244 data), R = 0.029 (2039 data with I > 2σI). CCDC # 639667. Copies of the crystal data can be obtained free of charge from CCDC, 12, Union Road, Cambridge CB2 1EZ, UK; fax: + 44 1223 336 033; e-mail: deposit@ccdc.cam.ac.uk.