Regioselective synthesis of new 5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene bromides and rearrangement reaction thereof
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(Z)-5-Substituted-2-alkylidene-4-oxothiazolidine derivatives 2a-c were regioselectively brominated to afford the new, synthetically useful vinyl bromides 3a-c, They undergo novel rearrangement reaction to provide 4-oxothiazolidine derivatives 5a-c containing two fully conjugated exocyclic double bonds. Extremely clean and efficient derivatization of 2a-c to 5a-c was also achieved by a one-pot three-step sequence under mild experimental conditions without isolation of vinyl bromides 3a-c.
Keywords:push-pull alkene / 4-oxothiazolidine derivatives / regioselective bromination / rearrangement reaction
Source:Synlett, 2000, 5, 607-610
- Georg Thieme Verlag, Stuttgart