A Dieckmann Cyclization Route to Piperazine-2,5-diones

作者：Aboussafy Claude Larrivee; Clive Derrick L J^*

来源：Journal of Organic Chemistry, 2012, 77(11): 5125-5131.

DOI：10.1021/jo3007144

Piperazine-2,5-diones are formed by Dieckmann cyclization (NaH, THF) of substructures of the type CH2-N(R)C(O)CH2N-(R')CO2Ph in which the terminal methylene (CH2) that is adjacent to nitrogen closes onto the carbonyl group of the phenyl carbamate unit at the other end of the chain. R and R' are alkyl groups, and the terminal methylene is activated by a ketone carbonyl, a nitrile, an ester, or a phosphoryl group. The starting materials are assembled by standard acylation and oxidation processes, starting from a beta-(alkylamino)alcohol, an (alkylamino)acetonitrile, an (alkylamino) ester, or an (alkylamino)methyl phosphonate.

• 出版日期2012-6-1