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Synlett 2012(1): 93-96  
DOI: 10.1055/s-0031-1290109
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© Georg Thieme Verlag Stuttgart ˙ New York

The Chemistry of α,β-Ditosyloxy Ketones: A New and Convenient Route to 4,5-Diarylisoxazoles from α,β-Chalcone Ditosylates

Raj Kamal*a, Deepak Sharmab, Deepak Wadhwaa, Om Prakasha
a Department of Chemistry, Kurukshetra University, Kurukshrtra 136119, Haryana, India
e-Mail: kamalraj_sharma@rediffmail.com;
b Govt. Post Graduate College, Ambala Cantt 133001, Haryana, India
Further Information

Publication History

Received 18 July 2011
Publication Date:
13 December 2011 (online)

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Abstract

The reaction of α,β-chalcone ditosylates with hydroxyl­amine hydrochloride under suitable conditions leads to a 1,2-aryl shift, thereby providing a new route to 4,5-disubstituted isoxazoles.

Key words

α,β-chalcone dibromides - α,β-chalcone ditosylates - hydroxy(tosyloxy)iodobenzene - 4,5-diarylisoxazoles

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9

Experimental procedure used to prepare α,β-chalcone ditosylates 1: Prepared from the corresponding chalcones¹7-²² 3 using a procedure similar to that reported previously by our research group. Compounds 1a-c,g,i-j,l were previously reported, whereas 1d-f,h,k,m-o are novel compounds. Spectroscopic data of the latter compounds are given in the Supporting Information.

11

Experimental procedure used to prepare 4,5-diaryl-isoxazoles 4: A mixture of chalcone ditosylate (1a; 0.550 g, 0.001 mol), hydroxylamine hydrochloride (0.138 g, 0.002 mol) and sodium acetate (0.164 g, 0.002 mol) in EtOH (25 mL) was heated at reflux for approximately 3 h. The reaction mixture was then poured onto ice-cold water. The resulting mixture was extracted with CH2Cl2 (3 × 50 mL) and the combined organic extract was dried over anhydrous Na2SO4 and filtered. Evaporation of CH2Cl2 in vacuo gave the crude product, which was purified by column chromatography on silica gel (100-200 mesh; PE-EtOAc) to give pure pyrazole 4a (72%, 0.159 g). Other derivatives were prepared in a similar manner. Compounds 4e,g,h,j,k,m-o are novel. Spectroscopic data of these compounds are given in the Supporting Information.