Synthetic route for the novel pyrimidine-substituted alkanoate, acetohydrazide, and imines: Synthon for [beta]-lactams

A simple and efficient synthesis of novel pyrimidine-substituted alkanoate, acetohydrazide, and imines is described. The synthesis of novel ethyl 2-(2,6-dimethylpyrimidin-4-yloxy)acetate (EDMPyA) 2 was performed through SN2 O-alkylation of 2,6-dimethyl-4-hydroxypyrimidine 1 with ethyl haloacetate. T...

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Bibliographic Details
Published in:Synthetic communications 2017-05, Vol.47 (10), p.982
Main Authors: Saini, Preety, Bari, Shamsher S, Banik, Bimal K, Bhalla, Aman
Format: Article
Language:English
Online Access:Get full text
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Summary:A simple and efficient synthesis of novel pyrimidine-substituted alkanoate, acetohydrazide, and imines is described. The synthesis of novel ethyl 2-(2,6-dimethylpyrimidin-4-yloxy)acetate (EDMPyA) 2 was performed through SN2 O-alkylation of 2,6-dimethyl-4-hydroxypyrimidine 1 with ethyl haloacetate. The compound EDMPyA 2 was subjected to nucleophilic substitution reaction with hydrazine hydrate to afford novel 2-(2,6-dimethylpyrimidin-4-yloxy)acetohydrazide (DMPyAH) 3. This DMPyAH 3 upon condensation with differently substituted carbonyl compounds (aldehydes/ketones) furnished DMPyAH imines (DMPyAH-I) 4a-d. These imines can be used for the preparation of unique [beta]-lactams. The structure elucidation of all the newly synthesized compounds was performed using spectroscopy (FT-IR, 1H and 13C NMR) and elemental analysis (C, H, N).
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2017.1301479