| Title |
Synthesis and characterization of novel methyl (3)5-(N-Boc-piperidinyl)-1H-pyrazole-4-carboxylates / |
| Authors |
Matulevičiūtė, Gita ; Arbačiauskienė, Eglė ; Kleizienė, Neringa ; Kederienė, Vilija ; Ragaitė, Greta ; Dagilienė, Miglė ; Bieliauskas, Aurimas ; Milišiūnaitė, Vaida ; Sløk, Frank A ; Šačkus, Algirdas |
| DOI |
10.3390/molecules26133808 |
| Full Text |
|
| Is Part of |
Molecules.. Basel : MDPI. 2021, vol. 26, iss. 13, art. no. 3808, p. 1-22.. ISSN 1420-3049 |
| Keywords [eng] |
building blocks ; enamines ; heterocyclic amino acids ; hydrazines ; piperidines ; pyrazoles ; β-keto esters |
| Abstract [eng] |
Series of methyl 3- and 5-(N-Boc-piperidinyl)-1H-pyrazole-4-carboxylates were developed and regioselectively synthesized as novel heterocyclic amino acids in their N-Boc protected ester form for achiral and chiral building blocks. In the first stage of the synthesis, piperidine-4-carboxylic and (R)- and (S)-piperidine-3-carboxylic acids were converted to the corresponding β-keto esters, which were then treated with N,N-dimethylformamide dimethyl acetal. The subsequent reaction of β-enamine diketones with various N-mono-substituted hydrazines afforded the target 5-(N-Boc-piperidinyl)-1H-pyrazole-4-carboxylates as major products, and tautomeric NH-pyrazoles prepared from hydrazine hydrate were further N-alkylated with alkyl halides to give 3-(N-Boc-piperidinyl)-1H-pyrazole-4-carboxylates. The structures of the novel heterocyclic compounds were confirmed by 1H-, 13C-, and 15N-NMR spectroscopy and HRMS investigation. |
| Published |
Basel : MDPI |
| Type |
Journal article |
| Language |
English |
| Publication date |
2021 |
| CC license |
|
