Generation and cycloaddition of polymer-supported azomethine imines: Traceless synthesis of pyrazole derivatives from α-silylnitrosoamide derivatives bound to resin

Tetrahedron Letters

Volumn 41, Issue 5, 2000, Pages 691-695

  Washizuka, Ken Ichi ^a   Nagai, Keiko ^a   Minakata, Satoshi ^a   Ryu, Ilhyong ^a   Komatsu, Mitsuo ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; DICARBOXYLIC ACID DERIVATIVE; IMINE; POLYMER; PYRAZOLE DERIVATIVE; RESIN;

ARTICLE; SYNTHESIS;

EID: 0034728120     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02140-1     Document Type: Article

References (41)

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40. 2O (10 mL×1) and dried in vacuo to give resin 13 (1.08 g). To a suspension of resin 13 (326 mg, 0.324 mmol) in toluene (3.2 mL) was added DMAD (160 μL, 1.30 mmol) and the mixture was then stirred at 110°C for 48 h. The reaction mixture was filtered and washed with toluene (10 mL×3). The filtrate was concentrated in vacuo and the residue was chromatographed on 10 g of silica gel (eluent: hexane:AcOEt=9:1 then 2:1) to give pyrazole (E)-14 (32.1 mg, 30%) and (Z)-14 (36.0 mg, 34%). The structure of (E)-14 was determined by spectral analysis and X-ray crystal structure determination.
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