235423-16-2Relevant academic research and scientific papers
Sequential bromination-rearrangement of push-pull thiazolidines induced by pyridinium hydrobromide perbromide under homogenous reaction conditions
Markovic, Rade,Baranac, Marija,Dzambaski, Zdravko
, p. 851 - 860 (2007/10/03)
Regiospecific bromination-rearrangement of the 5-substituted 2-alkylidene-4-oxothiazolidine derivatives induced by pyridinium hydrobromide perbromide (PHBP) provides a new synthetic approach to the corresponding push-pull thiazolidines with two exocyclic
Stereo- and regiocontrol of electrophile-initiated rearrangement of push-pull 5-substituted 4-oxothiazolidine derivatives
Markovi?, Rade,D?ambaski, Zdravko,Baranac, Marija
, p. 5833 - 5841 (2007/10/03)
Regioselective α-bromination of (Z)-5-substituted-2-alkylidene-4-oxothiazolidine derivatives affords, under mild experimental conditions, vinyl bromides 3 in good yields. They undergo rearrangement providing a highly efficient route to the stereodefined 4-oxothiazolidine derivatives possessing two fully delocalized exocyclic double bonds at C(2) and C(5) positions. A mechanism of this novel rearrangement reaction via base-promoted proton transfer from one carbanionic site to another, followed by the bromination-dehydrobromination sequence, is proposed.
Regioselective synthesis of new 5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene bromides and rearrangement reaction thereof
Markovi?, Rade,Baranac, Marija
, p. 607 - 610 (2007/10/03)
(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. Thieme Stuttgart.
