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Ring opening of cyclic thioimidates in reaction with active methylene compounds

Tetrahedron 2015, 71 (40), 7567-7574

DOI: 10.1016/j.tet.2015.08.009

Shvydenko K.; Nazarenko K.; Shvydenko T.; Vlasenko Y.; Tolmachev A.; Kostyuk A.

The reaction of cyclic thioimidates with active methylene compounds in the presence of acetic acid anhydride was studied. In case of six- and seven-membered derivatives the reaction proceeded via substitution of thiomethoxy group affording cyclic enamines. In case of five-membered derivatives the reaction proceeded via opening of the thioimidate ring affording functionalized aminopropane derivatives.

Ring opening of cyclic thioimidates in reaction with active methylene compounds

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