Microwave-Assisted One-Pot Synthesis
of Pyrazolo[3,4-b]indoles
and New Isoxazolo[5,4-b]indoles
via Copper-Catalyzed Intramolecular C-N/C-O
Bond Formation

Arepalli Sateesh Kumar; P. V. Amulya Rao; Rajagopal Nagarajan

doi:10.1055/s-0031-1289572

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

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synthesis 2011(23): 3878-3886
DOI: 10.1055/s-0031-1289572

PAPER

Microwave-Assisted One-Pot Synthesis of Pyrazolo[3,4-b]indoles and New Isoxazolo[5,4-b]indoles via Copper-Catalyzed Intramolecular C-N/C-O Bond Formation

Arepalli Sateesh Kumar, P. V. Amulya Rao, Rajagopal Nagarajan*
School of Chemistry, University of Hyderabad, Hyderabad 500 046, India
Fax: +91(40)23012460; e-Mail: rnsc@uohyd.ernet.in;

Further Information

Publication History

Received 1 August 2011
Publication Date:
21 October 2011 (online)

Abstract
Full Text
References
Supplementary Material

Permissions and Reprints All articles of this category

Abstract

A facile one-pot, two-step synthesis of highly substituted pyrazolo[3,4-b]indoles and isoxazolo[5,4-b]indoles was developed via microwave-assisted, copper-catalyzed intramolecular heterocyclization (involving C-N/C-O bond formation) from 3-acetyl-2-chloroindoles in good to excellent yields.

Key words

copper catalysis - 3-acyl-2-chloroindoles - pyrazolo[3,4-b]indoles - isoxazolo[5,4-b]indoles - intramolecular heteroarylation

Supporting Information

Primary Data

References

1 Elguero J. Goya P. Jagerovic N. Silva AMS. Targets Heterocycl. Syst. 2002, 6: 52

Google Scholar
2 Penning TD. Talley JJ. Bertenshaw SR. Carter JS. Collins PW. Docter S. Graneto MJ. Lee LF. Malecha JW. Miyashiro JM. Rogers RS. Rogier DJ. Yu SS. Anderson GD. Burton EG. Cogburn JN. Gregory SA. Koboldt CM. Perkins WE. Seibert K. Veenhuizen AW. Zhang YY. Isakson PC. J. Med. Chem. 1997, 40: 1347

Google Scholar
3 Terrett NK. Bell AS. Brown D. Ellis P. Bioorg. Med. Chem. Lett. 1996, 6: 1819

Google Scholar
For reviews, see:
4a Carlsen L. Döpp D. Döpp H. Duus F. Hartmann H. Lang-Fugmann S. Schulze B. Smalley RK. Wakefield BJ. In Houben-Weyl Methods of Organic Chemistry Vol. E8a: Schaumann E. Georg Thieme; Stuttgart: 1992. p.45-204

Google Scholar
4b Sperry J. Wright D. Curr. Opin. Drug Discovery Dev. 2005, 8: 723

Google Scholar
5a Knölker H.-J. Reddy KR. In The Alkaloids Vol. 65: Cordell GA. Academic Press; Amsterdam: 2008. p.1

Google Scholar
5b Sundberg RJ. The Chemistry of Indoles Academic Press; New York: 1970.

Google Scholar
5c Sundberg RJ. Pyrroles and Their Benzo Derivatives: Synthesis and Applications, In Comprehensive Heterocyclic Chemistry Vol. 4: Katritzky AR. Rees CW. Pergamon Press; Oxford: 1984. p.313-376

Google Scholar
5d Joule J. A.; Indole and Its Derivatives, In Science of Synthesis, Houben-Weyl Methods of Molecular Transformations; Thomas E. J.; George Thieme: Stuttgart, 2000; Vol. 10: 361-652
5e Gribble GW. In Comprehensive Heterocyclic Chemistry II Vol. 2: Katritzky AR. Rees CW. Scriven EFV. Bird CW. Pergamon Press; Oxford: 1996. p.207

Google Scholar
For some recent methods, see:
6a Knölker H.-J. Reddy KR. Chem. Rev. 2002, 102: 4303

Google Scholar
6b Smith AB. Kürti L. Davulcu AH. Org. Lett. 2006, 8: 2167

Google Scholar
6c Knölker H.-J. Chem. Lett. 2009, 38: 8

Google Scholar
6d Smith AB. Kanoh N. Minakawa N. Rainier JD. Blase FR. Hartz RA. Org. Lett. 1999, 1: 1263

Google Scholar
6e Liu J. Shen M. Zhang Y. Li G. Khodabocus A. Rodriguez S. Qu B. Farina V. Senanayake CH. Lu BZ. Org. Lett. 2006, 8: 3573

Google Scholar
6f Roesch KR. Larock RC. Org. Lett. 1999, 1: 1551

Google Scholar
6g Kusama H. Takaya J. Iwasawa N. J. Am. Chem. Soc. 2002, 124: 11592

Google Scholar
6h Battistuzzi G. Cacchi S. Fabrizi G. Marinelli F. Parisi LM. Org. Lett. 2002, 4: 1355

Google Scholar
6i Müller TE. Beller M. Chem. Rev. 1998, 98: 675

Google Scholar
6j Beller M. Breindl C. Riermeier TH. Eichberger M. Trauthwein H. Angew. Chem. Int. Ed. 1998, 37: 3389

Google Scholar
6k Witulski B. Stengel T. Angew. Chem. Int. Ed. 1999, 38: 2426

Google Scholar
6l Kondo Y. Kojima S. Sakamoto T. J. Org. Chem. 1997, 62: 6507

Google Scholar
6m Coleman RS. Chen W. Org. Lett. 2001, 3: 1141

Google Scholar
6n Watanabe M. Yamamoto T. Nishiyama M. Angew. Chem. Int. Ed. 2000, 39: 2501

Google Scholar
6o Takeda A. Kamijo S. Yamamoto Y. J. Am. Chem. Soc. 2000, 122: 5662

Google Scholar
6p Wagaw S. Yang BH. Buchwald SL. J. Am. Chem. Soc. 1999, 121: 10251

Google Scholar
6q Koradin C. Dohle W. Rodriguez AL. Schmid B. Knochel P. Tetrahedron 2003, 59: 1571

Google Scholar
6r Köhling P. Schmidt AM. Eilbracht P. Org. Lett. 2003, 5: 3213

Google Scholar
6s Knepper K. Bräse S. Org. Lett. 2003, 5: 2829

Google Scholar
6t Barluenga J. Pure Appl. Chem. 2002, 74: 1317

Google Scholar
6u Knölker H.-J. Curr. Org. Synth. 2004, 1: 309

Google Scholar
7a Ziegler FE. Jeroncic LO. J. Org. Chem. 1991, 56: 3479

Google Scholar
7b Markgraf JH. Snyder SA. Vosburg DA. Tetrahedron Lett. 1998, 39: 1111

Google Scholar
7c Colandrea VJ. Rajaraman S. Jimenez L. Org. Lett. 2003, 5: 785

Google Scholar
7d Vigushin DM. Brooke G. Willows D. Coobes RC. Moody CJ. Bioorg. Med. Chem. Lett. 2003, 13: 3661

Google Scholar
7e Coleman RS. Felpin FX. Chen W. J. Org. Chem. 2004, 69: 7309

Google Scholar
8a Metal-Catalyzed Cross-Coupling Reactions de Meijere A. Diedrich F. Wiley-VCH; Weinheim: 2004.

Google Scholar
8b Tsuji J. Palladium in Organic Synthesis Springer; Berlin: 2005.

Google Scholar
8c Handbook of Organopalladium Chemistry for Organic Synthesis Negishi E.-i. de Meijere A. Wiley-Interscience; New York: 2002.

Google Scholar
9 Ullmann F. Bielecki J. Ber. Dtsch. Chem. Ges. 1901, 34: 2174

Google Scholar
10 Ullmann F. Ber. Dtsch. Chem. Ges. 1903, 36: 2382

Google Scholar
11 Ma D. Zhang Y. Yao J. Wu S. Tao F. J. Am. Chem. Soc. 1998, 120: 12459

Google Scholar
For some recent reviews, see:
12a Monnier F. Taillefer M. Angew. Chem. Int. Ed. 2009, 48: 6954

Google Scholar
12b Corbet JP. Mignani G. Chem. Rev. 2006, 106: 2651

Google Scholar
12c Evano G. Blanchard N. Toumi M. Chem. Rev. 2008, 108: 3054

Google Scholar
12d Correa A. Mancheno OG. Bolm C. Chem. Soc. Rev. 2008, 37: 1108

Google Scholar
12e Wurtz S. Glorius F. Acc. Chem. Res. 2008, 41: 1523

Google Scholar
12f Hartwig JF. Synlett 2006, 1283

Google Scholar
12g Beletskaya IP. Cheprakov AV. Coord. Chem. Rev. 2004, 248: 2337

Google Scholar
For some examples of C-N cross-coupling, see:
13a Brasche G. Buchwald SL. Angew. Chem. Int. Ed. 2008, 47: 1932

Google Scholar
13b Tsang WCP. Zheng N. Buchwald SL. J. Am. Chem. Soc. 2005, 127: 14560

Google Scholar
13c Inamoto K. Saito T. Katsuno M. Sakamoto T. Hiroya K. Org. Lett. 2007, 9: 2931

Google Scholar
13d Meesala R. Nagarajan R. Tetrahedron 2009, 65: 6050

Google Scholar
For examples of C-O cross-coupling, see:
14a Ueda S. Nagasawa H. J. Org. Chem. 2009, 74: 4272

Google Scholar
14b Wang W. Luo F. Zhang S. Cheng J. J. Org. Chem. 2010, 75: 2415

Google Scholar
14c Guru MM. Ali MA. Punniyamurthy T. Org. Lett. 2011, 13: 1194

Google Scholar
14d Rao H. Fu H. Synlett 2011, 745

Google Scholar
15a Lande B. Soufiaoui M. Arriau J. J. Heterocycl. Chem. 1977, 14: 1183

Google Scholar
15b Daou B. Soufiaoui M. J. Heterocycl. Chem. 1989, 26: 1485

Google Scholar
15c Williams JD. Drach JC. Townsend LB. Nucleosides, Nucleotides Nucleic Acids 2004, 23: 805

Google Scholar
15d Monge A. Palop J. Ramirez C. Font M. Fernandez-Alvarez E. Eur. J. Med. Chem. 1991, 26: 179

Google Scholar
16 Kumar S. Ila H. Junjappa H. J. Org. Chem. 2009, 74: 7046

Google Scholar
For reviews, see:
17a Larhed M. Moberg C. Hallberg A. Acc. Chem. Res. 2002, 35: 717

Google Scholar
17b Lew A. Krutzik PO. Hart ME. Chamberlin AR. J. Comb. Chem. 2002, 4: 95

Google Scholar
17c Lidström P. Tierney J. Wathey B. Westman J. Tetrahedron 2001, 57: 9225

Google Scholar
17d Perreux L. Loupy A. Tetrahedron 2001, 57: 9199

Google Scholar

18

The crystal data of compound 2a have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 832662. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax:
+44 (1223)336033; E-mail: deposit@ccdc.cam.ac.uk] or via www.ccdc.cam.ac.uk/data_request/cif.
Compound 2a: C₁₆H₁₃N₃, M = 247.29; unit cell parameters: a = 13.2646(12) Å, b = 14.7200(13) Å, c = 15.4448(14) Å, α = 104.423(2)˚, β = 107.550(2)˚, γ = 112.102(2)˚, space group P1.

Supplementary Material
Primary Data

Supporting Information

Primary Data