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Synthesis 2012; 44(15): 2401-2407
DOI: 10.1055/s-0031-1289789
paper
© Georg Thieme Verlag Stuttgart · New York

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

Alexander V. Sapegin
a   The Ushinsky Yaroslavl State Pedagogical University, 108 Respublikanskaya St., Yaroslavl, 150000, Russian Federation
,
Stanislav A. Kalinin
a   The Ushinsky Yaroslavl State Pedagogical University, 108 Respublikanskaya St., Yaroslavl, 150000, Russian Federation
,
Alexey V. Smirnov
a   The Ushinsky Yaroslavl State Pedagogical University, 108 Respublikanskaya St., Yaroslavl, 150000, Russian Federation
,
Mikhail V. Dorogov
a   The Ushinsky Yaroslavl State Pedagogical University, 108 Respublikanskaya St., Yaroslavl, 150000, Russian Federation
,
Mikhail Krasavin*
b   Eskitis Institute for Cell and Molecular Therapies, Griffith University, Nathan, Queensland 4111, Australia, Fax: +61(7)37356001   Email: m.krasavin@griffith.edu.au
› Author Affiliations
Further Information

Publication History

Received: 15 March 2012

Accepted after revision: 11 May 2012

Publication Date:
20 June 2012 (online)

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Abstract

Condensation of 2-(1H-pyrazol-5-yl)phenols with 1-chloro-2-nitrobenzenes under basic conditions in N,N-dimethyl­formamide 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.

Key words

tetracyclic scaffolds - privileged structures - atom-economical­ syntheses - dibenzo[b,f][1,4]oxazepines - Smiles rearrangement - nucleophilic aromatic substitution - denitrocyclization - regiospecific reaction

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    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
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