Synthesis and Ring-Chain-Ring Tautomerism of Bisoxazolidines, Thiazolidinyloxazolidines, and Spirothiazolidines
journal contributionposted on 15.07.2011, 00:00 authored by Cecilia Saiz, Peter Wipf, Graciela Mahler
The synthesis of fused heterocycles such as thiazolidinyl-oxazolidine 3 is described starting from Tris·HCl. The mercaptomethyl bisoxazolidine 8 was found to convert to the corresponding thiazolidinyloxazolidine 3 and the spiro-heterocycle 4 by a ring-chain-ring tautomerism, depending on the electronic nature of the ring substituents as well as the reaction conditions. This equilibration pathway is absent in the hydroxymethyl bisoxazolidines 2. Computational studies confirm that both kinetic and thermodynamic control features play a role in the product distribution.
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reaction conditionsThiazolidinyloxazolidineTautomerismmercaptomethyl bisoxazolidine 8ring substituentsrolecontrol featurestautomerismheterocyclenatureBisoxazolidineproduct distributionequilibration pathwaythiazolidinyloxazolidine 3SpirothiazolidinesThe synthesishydroxymethyl bisoxazolidines 2. Computational studiesSynthesiTris