Construction of novel spiroisoxazolines via intramolecular cyclization/methylation

Tetrahedron Letters

Volumn 50, Issue 39, 2009, Pages 5516-5519

  Ellis, Erick D ^a   Xu, Jianping ^a   Valente, Edward J ^b   Hamme II, Ashton T ^a  

^a Jackson State University   (United States)

^b UNIVERSITY OF PORTLAND   (United States)

Author keywords

Cycloaddition; Heterocycles; Intramolecular cyclization; Regioselectivity; Spirocycles

Indexed keywords

ISOXAZOLINE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 68349148072     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.07.095     Document Type: Article

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33. General procedure for 1,3-dipolar cycloaddition: A solution of the alkene (3.0 mmol) and the hydroximoyl chloride (3.0 mmol) in 4 mL of dichloromethane was heated to 50 °C for 10 min. Triethylamine (0.46 mL, 3.3 mmol) was then added dropwise, and the resulting reaction mixture was heated for an additional 5 min at 50 °C. The reaction mixture was stirred at rt until the disappearance of the starting materials, as evidenced by TLC. After the reaction was complete, the reaction mixture was washed with water (3 × 4 mL) and brine (4 mL). The organic layer was dried over anhydrous sodium sulfate, filtered, and the solvent was evaporated under reduced pressure. Based upon TLC and NMR, no purification was necessary, and the crude products were used in the subsequent step.
34. 4OH (1 mL) was added, and the mixture was stirred for 30 min to 3 h. The reaction mixture was washed with water (3 × 5 mL), and the organic layer was dried over anhydrous sodium sulfate, filtered, and the solvent was evaporated under reduced pressure. The crude product was purified via column chromatography over silica gel using a 2:1 hexanes-ethyl acetate as an eluant system.
35. Structural information for 5c and 6c has been deposited with the CCDC as 738659 and 739766, respectively, available free of charge from www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033).