183367-31-9Relevant academic research and scientific papers
Enantioselective synthesis of 5-methylidenedihydrouracils as potential anticancer agents
Pi?ta, Marlena,K?dzia, Jacek,Kowalczyk, Dorota,Wojciechowski, Jakub,Wolf, Wojciech M.,Janecki, Tomasz
, p. 2495 - 2505 (2019)
An efficient, versatile, enantioselective synthesis of 1,3-disubstituted and 1,3,6-trisubstituted 5-methylidenedihydrouracils applying Horner-Wadsworth Emmons methodology was developed. Starting 1,3-disubstituted 5-diethoxyphosphoryluracils were subjected
N,N-cyclization of carbodiimides with 2-(bromomethyl)acrylic acid. a direct entry to the system 5-methylene-6H-pyrimidine-2,4-dione, a new class of thymine analogues
Anglada,Campos,Camps,Moreto,Pages
, p. 1259 - 1270 (2007/10/03)
Carbodiimides react under very mild conditions with 2-(bromomethyl)acrylic acid at both N atoms to give 1,3-disubstituted-5-methylene-6ff-pyrimidine 2,4-dione derivatives in moderate to good yields. These products behaved as good Michael acceptors towards a variety of nucleophiles such as bromine, hydrochloric acid, hydrides, etc. A plausible mechanism is proposed based on theoretical approaches and experimental results.
