A Simple Synthesis of Polyfunctionalized 4‐Aminopyrazolidin‐3‐ones as ‘Aza‐deoxa’ Analogs of D‐Cycloserine |
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| Authors: | Ana Novak Matej Štefanič Uroš Grošelj Martina Hrast Marta Kasunič Stanislav Gobec Branko Stanovnik Jurij Svete |
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| Affiliation: | 1. Faculty of Chemistry and Chemical Technology, University of Ljubljana, A?ker?eva 5, SI‐1000 Ljubljana (phone: +386‐1‐2419254;2. fax: +386‐1‐2419220);3. Faculty of Pharmacy, University of Ljubljana, A?ker?eva 7, SI‐1000 Ljubljana;4. Centre of Excellence EN‐FIST, Trg osvobodilne fronte 13, SI‐1000 Ljubljana |
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| 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 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. |
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| Keywords: | Amino acids D‐Cycloserine Pyrazolidin‐3‐ones, 4‐amino‐ Hydrogenation, catalytic Alkylation, reductive Catalysis |
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