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Synthesis 2011(23): 3878-3886  
DOI: 10.1055/s-0031-1289572
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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;
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Publication History

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

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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

    Primary data for this article are available online at http­://www.thieme-connect.com/ejournals/toc/synthesis and can be cited using the following DOI: 10.4125/pd0020th.
  • Primary Data (ZIP)

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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.