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A Simple Synthesis of Polyfunctionalized 4‐Aminopyrazolidin‐3‐ones as ‘Aza‐deoxa’ Analogs of D ‐Cycloserine
Author(s) -
Novak Ana,
Štefanič Matej,
Grošelj Uroš,
Hrast Martina,
Kasunič Marta,
Gobec Stanislav,
Stanovnik Branko,
Svete Jurij
Publication year - 2014
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201300169
Subject(s) - chemistry , alkylation , halide , reagent , alkyl , nuclear magnetic resonance spectroscopy , combinatorial chemistry , stereochemistry , organic chemistry , catalysis
A simple five‐step synthesis of fully substituted (4 RS ,5 RS )‐4‐aminopyrazolidin‐3‐ones as analogs of D ‐cycloserine was developed. It comprises a two‐step preparation of 5‐substituted (4 RS ,5 RS )‐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 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.