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Issue 2, 2019
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A simple route to tetracyclic oxazepine-fused pyrroles via metal-free [3+2] annulation between dibenzo[b,f][1,4]oxazepines and aqueous succinaldehyde

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Abstract

A direct method for the synthesis of new tetracyclic oxazepine-fused pyrroles has been developed through [3+2] annulation between aqueous succinaldehyde and dibenzo[b,f][1,4]-oxazepines under metal-free conditions. This one-pot synthetic protocol involves proline-catalyzed direct Mannich/cyclization between aqueous succinaldehyde and seven-membered oxazepine-imines, followed by an IBX-mediated oxidation sequence with high yields (up to 90%).

Graphical abstract: A simple route to tetracyclic oxazepine-fused pyrroles via metal-free [3+2] annulation between dibenzo[b,f][1,4]oxazepines and aqueous succinaldehyde

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Publication details

The article was received on 25 Sep 2018, accepted on 05 Nov 2018 and first published on 06 Nov 2018


Article type: Paper
DOI: 10.1039/C8NJ04861D
Citation: New J. Chem., 2019,43, 953-962
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    A simple route to tetracyclic oxazepine-fused pyrroles via metal-free [3+2] annulation between dibenzo[b,f][1,4]oxazepines and aqueous succinaldehyde

    S. Choudhary, A. Singh, J. Yadav, N. A. Mir, S. Anthal, R. Kant and I. Kumar, New J. Chem., 2019, 43, 953
    DOI: 10.1039/C8NJ04861D

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