285133-46-2

Upstream product

• 204690-21-1 (Z)-(5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene)-N-phenylethanamide 

Downstream Products

• 235423-16-2 (2Z,5Z)-N-phenyl (5-ethoxycarbonylmethylidene-4-oxothiazolidin-2-ylidene)ethanamide 
• 235423-20-8 (2E,5Z)-N-phenyl (5-ethoxycarbonylmethylidene-4-oxothiazolidin-2-ylidene)ethanamide 
• 285133-47-3 (Z)-2-bromo-2-(5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene)-N-phenylethanamide 

Relevant academic research and scientific papers

Stereo- and regiocontrol of electrophile-initiated rearrangement of push-pull 5-substituted 4-oxothiazolidine derivatives

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

(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.