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

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.

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

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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:
[phone]; E-mail: [e-mail]] 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.