A Simple Synthesis of Polyfunctionalized 4??Aminopyrazolidin??3??ones as 'Aza??deoxa'Analogs of D??Cycloserine

…, M Kasunič, S Gobec, B Stanovnik, J Svete

Index: Novak, Ana; Stefanic, Matej; Groselj, Uros; Hrast, Martina; Kasunic, Marta; Gobec, Stanislav; Stanovnik, Branko; Svete, Jurij Helvetica Chimica Acta, 2014 , vol. 97, # 2 p. 245 - 267

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Citation Number: 2

Abstract

Abstract A simple five-step synthesis of fully substituted (4RS, 5RS)-4-aminopyrazolidin-3- ones as analogs of D-cycloserine was developed. It comprises a two-step preparation of 5- substituted (4RS, 5RS)-4-(benzyloxycarbonylamino) pyrazolidin-3-ones, reductive alkylation at N (1), alkylation of the amidic N (2) with alkyl halides, and simultaneous hydrogenolytic deprotection/reductive alkylation of the primary NH 2 group. The synthesis enables an ...