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Synthesis 2009(16): 2741-2748  
DOI: 10.1055/s-0029-1216875
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 2,1-Benzisoxazoles by Nucleophilic Substitution of Hydrogen in Nitroarenes Activated by the Azole Ring

Nazariy T. Pokhodylo*, Yuriy O. Teslenko, Vasyl S. Matiychuk, Mykola D. Obushak
Department of Organic Chemistry, Ivan Franko National University of Lviv, Kyryla i Mefodiya St. 6, Lviv 79005, Ukraine
Fax: +38(32)2971668; e-Mail: pokhodylo@gmail.com;
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Publication History

Received 15 April 2009
Publication Date:
26 June 2009 (online)

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Abstract

Reaction of 1-nitro-4-(1,2,3-triazolyl/tetrazolyl)benzenes with arylacetonitriles in an alcoholic medium in the presence of excess alkali gives novel 2,1-benzisoxazoles. These findings indicate a high reactivity of nitroarenes activated by the azole ring due to their electron-deficient character. Moreover, it was found that annulation of the isoxazole ring occurred regioselectively in disubstituted nitroarenes. In the case of 1-(4-nitrophenyl)-1H-tetrazole, the tetrazole ring cleaved faster than the σH-adduct was formed.

Key words

1H-1,2,3-triazole - tetrazole - nucleophilic substitution - 2,1-benzisoxazole - annulation

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