Tetrahedron p. 3585 - 3590 (1980)
Update date:2022-08-02
Topics:
Carlsson, S.
Lawesson, S.-O.
Enamines (1) derived from cyclohexanone or cyclopentanone are reacted with electrophilic olefins (ethyl acrylate, ethyl 2-methylacrylate, ethyl 2-butenoate) to give the new enamines, 2.When 2 is reacted with LiAlH4, reductive cyclisation takes place giving hexahydrochromane-8a-amines of octahydrocyclopentapyrane-7a-amines, 3, in quantitative yields, 3 is hydrolyzed with dilute aqueous hydrochloric acid to hexahydrochromane-8a-ols of octahydrocyclopentapyrane-7a-ols (4) and reacts also with oxalic acid in refluxing dioxane to form the condensed dihydropyranes, 5.
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