Dibenzo[b,f]pyrazolo[1,5-d][1,4]oxazepines: facile construction of a rare heterocyclic system via tandem aromatic nucleophilic substitution - Smiles rearrangement – denitrocyclization

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V. Sapegin, Alexander
A. Kalinin, Stanislav
V. Smirnov, Alexey
V. Dorogov, Mikhail
Krasavin, Mikhail
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2012
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Abstract

Condensation of 2-(1H-pyrazol-5-yl)phenols with 1-chloro-2-nitrobenzenes under basic conditions in N,N-dimethylforrmamide results in a tandem, atom-economical, aromatic nucleophilic substitution-Smiles rearrangement-denitrocyclization process to provide pyrazolo-fused dibenzo[b,f][1,4]oxazepines as a single regioisomer.

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Synthesis: Journal of Synthetic Organic Chemistry

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44

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© 2012 Georg Thieme Verlag. This is the author-manuscript version of the paper. Reproduced in accordance with the copyright policy of the publisher. The definitive version is available at www.thieme-connect.com

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Medicinal and Biomolecular Chemistry not elsewhere classified

Analytical Chemistry

Organic Chemistry

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