New synthesis of the amino acid (+-)-cucurbitine was written by Monteiro, Hugo J.. And the article was included in Journal of the Chemical Society, Chemical Communications in 1973.Application In Synthesis of Ethyl 2,3-dioxopiperidine-4-carboxylate The following contents are mentioned in the article:
Bromination of Et 2,3-dioxo-4-piperidine carboxylate (I; X = H) gave 95% of the 4-bromo derivative (I; X = Br) which with NaN3 in refluxing MeO(CH2)2OMe gave 80% of the azido derivative (I; X = N3). I (X = Br, N3) in CHCl3 with AcOOH underwent ring contraction to 60-80% of the corresponding oxopyrrolidines (II; R = O). II (X = N3, R = O) with Et3O+BF4- gave the imino ether (III). Quant. B2H6 reduction of III gave 40% of the azidopyrrolidine (II; X = N3, R = H2), which underwent catalytic hydrogenation (PtO2) to give (±)-cucurbitine Et ester (II; X = NH2, R = H2) which on hydrolysis gave 70% (±)-cucurbitine. This study involved multiple reactions and reactants, such as Ethyl 2,3-dioxopiperidine-4-carboxylate (cas: 30727-21-0Application In Synthesis of Ethyl 2,3-dioxopiperidine-4-carboxylate).
Ethyl 2,3-dioxopiperidine-4-carboxylate (cas: 30727-21-0) belongs to piperidine derivatives. The piperidine moiety constitutes an important building block for the synthesis of a variety of bioactive natural products, alkaloids and other drugs. Several piperidine alkaloids isolated from natural herbs, were found to exhibit antiproliferation and antimetastatic effects on various types of cancers both in vitro and in vivo for example Piperine, Evodiamine, Matrine, Berberine and Tetrandine.Application In Synthesis of Ethyl 2,3-dioxopiperidine-4-carboxylate
Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem