A Simple Synthesis of Polyfunctionalized 4‐Aminopyrazolidin‐3‐ones as 'Aza‐deoxa' Analogs of D‐Cycloserine. Issue 2 (February 2014)

• Record Type: Journal Article
• Authors: Novak, Ana; Štefanič, Matej; Grošelj, Uroš; Hrast, Martina; Kasunič, Marta; Gobec, Stanislav; Stanovnik, Branko; Svete, Jurij
• Is Part Of: Helvetica chimica acta. Volume 97:Issue 2(2014:Feb.)
• Page Start: 245
• Page End: 267
• Publication Date: 2014-02
• Subjects: Chemistry -- Periodicals; Chemistry, Analytical -- periodicals; Chimie -- Périodiques; 540
• DOI: 10.1002/hlca.201300169
• Languages: English
• ISSNs: 0018-019X

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>A simple five‐step synthesis of fully substituted (4<italic>RS</italic>, 5<italic>RS</italic>)‐4‐aminopyrazolidin‐3‐ones as analogs of <sc>D</sc>‐cycloserine was developed. It comprises a two‐step preparation of 5‐substituted (4<italic>RS</italic>, 5<italic>RS</italic>)‐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 NH₂ group. The synthesis enables an easy stepwise functionalization of the pyrazolidin‐3‐one core with only two types of common reagents, aldehydes (or ketones) and alkyl halides. The structures of products were elucidated by NMR spectroscopy and X‐ray diffraction.</p> </abstract>