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General procedure for the synthesis of [2+3]-cycloaddition products: A solution of the functionalized alkene (3.0 mmol) and the hydrazonyl chloride (3.0 mmol) in 10 mL of either dry chloroform or dichloromethane was treated with triethylamine (0.463 mL, 3.3 mmol). The reaction mixture was stirred at rt until the disappearance of the starting materials, as evidenced by TLC. After the reaction was complete, the crude reaction mixture was concentrated, and the solvent was evaporated under reduced pressure. The crude products were purified by flash column chromatography over silica gel by using the appropriate hexanes-ethyl acetate ratio as an eluant system.
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note
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General procedure for the intramolecular cyclization/alkylation: To a solution of the cycloaddition product (1.0 mmol) in 15 mL of anhydrous toluene was added potassium tert-butoxide (6-8 mmol). The reaction mixture was then allowed to stir under anhydrous conditions until the disappearance of the starting materials, as evidenced by TLC. To this mixture was added 2 equiv of dimethyl sulfate (2 mmol, 0.186 mL), and the reaction mixture was heated to reflux temperature for 8 h under anhydrous conditions. The reaction mixture was later quenched with saturated ammonium chloride and extracted with EtOAc. The crude reaction mixture was concentrated, and the solvent was evaporated under reduced pressure. The crude products were purified by flash column chromatography over silica gel by using the appropriate hexanes-ethyl acetate ratio as an eluant system.
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