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Synlett 2011(1): 99-103  
DOI: 10.1055/s-0030-1259081
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Benzotriazole Analogues of the Helicobactericidal Agents CJ-13,015, CJ-13,102, CJ-13,108, and CJ-13,104 Using a Regioselective 1,3-Dipolar Cycloaddition

Darcy J. Atkinsona,b, Jonathan Sperrya,b, Margaret A. Brimble*a,b
a Department of Chemistry, University of Auckland, 23 Symonds Street, Auckland, New Zealand
b Maurice Wilkins Centre for Molecular Biodiscovery, University of Auckland, Auckland, New Zealand
Fax: +64(9)3737422; e-Mail: m.brimble@auckland.ac.nz;
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Publication History

Received 19 October 2010
Publication Date:
07 December 2010 (online)

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Abstract

A regioselective 1,3-dipolar cycloaddition of a disubstituted aryne and various alkyl azides facilitates access to benzotri­azole analogues of several anti-Helicobacter pylori antibiotics.

Key words

benzotriazole - helicobacter pylori - benzyne - dipolar cycloaddition

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General Procedure for the Synthesis of Benzotriazole Analogues of the CJ Compounds
To a stirred solution of azide (0.3 mmol) in MeCN (6 mL) was added CsF (0.6 mmol, 2 equiv) and 18-crown-6 (0.6 mmol, 2 equiv), and the reaction mixture was stirred at r.t. for 15 min. A solution of benzyne precursor 39 (0.6 mmol,
2 equiv) in MeCN (2 mL) was added dropwise, and the reaction mixture was stirred until completion (1.5-5 h). Aqueous NaHCO3 (10 mL) was added, and the reaction mixture was extracted with CH2Cl2 (5 × 5 mL). The combined organic extracts were dried over MgSO4, filtered, and the solvent removed under reduced pressure. The resulting residue was purified by flash chromatography using hexanes-EtOAc as eluent to afford the desired benzotriazole (Table  [¹] ).