Display options
Cite
Šenica L, Stopar K, Friedrich M, et al. Synthesis and Rotational Isomerism of 1-Substituted Methyl (S)-[5-(2-Nitrophenyl)-1H-pyrazole-4-carbonyl]alaninates. J Org Chem. 2015;81(1):146-61doi: 10.1021/acs.joc.5b02467.
Šenica, L., Stopar, K., Friedrich, M., Grošelj, U., Plavec, J., Počkaj, M., Podlipnik, �. �., Štefane, B., & Svete, J. (2016). Synthesis and Rotational Isomerism of 1-Substituted Methyl (S)-[5-(2-Nitrophenyl)-1H-pyrazole-4-carbonyl]alaninates. The Journal of organic chemistry, 81(1), 146-61. https://doi.org/10.1021/acs.joc.5b02467
Šenica, Luka, et al. "Synthesis and Rotational Isomerism of 1-Substituted Methyl (S)-[5-(2-Nitrophenyl)-1H-pyrazole-4-carbonyl]alaninates." The Journal of organic chemistry vol. 81,1 (2016): 146-61. doi: https://doi.org/10.1021/acs.joc.5b02467
Šenica L, Stopar K, Friedrich M, Grošelj U, Plavec J, Počkaj M, Podlipnik Č, Štefane B, Svete J. Synthesis and Rotational Isomerism of 1-Substituted Methyl (S)-[5-(2-Nitrophenyl)-1H-pyrazole-4-carbonyl]alaninates. J Org Chem. 2016 Jan 04;81(1):146-61. doi: 10.1021/acs.joc.5b02467. Epub 2015 Dec 19. PMID: 26649855.
Copy Download .nbib Format: NLM
Share it on

J Org Chem. 2016 Jan 04;81(1):146-61. doi: 10.1021/acs.joc.5b02467. Epub 2015 Dec 19.

Synthesis and Rotational Isomerism of 1-Substituted Methyl (S)-[5-(2-Nitrophenyl)-1H-pyrazole-4-carbonyl]alaninates.

The Journal of organic chemistry

Luka Šenica, Karmen Stopar, Miha Friedrich, Uroš Grošelj, Janez Plavec, Marta Počkaj, Črtomir Podlipnik, Bogdan Štefane, Jurij Svete

Affiliations

  1. Faculty of Chemistry and Chemical Technology, University of Ljubljana , Ve?na pot 113, SI-1000 Ljubljana, Slovenia.
  2. Centre of Excellence EN-FIST , Trg Osvobodilne fronte 13, SI-1000 Ljubljana, Slovenia.
  3. National Institute of Chemistry , Hajdrihova 19, SI-1000 Ljubljana, Slovenia.

PMID: 26649855 DOI: 10.1021/acs.joc.5b02467

Abstract

Seven title compounds 12a-g and the (S)-prolinate analogue 13 were prepared in five steps from 2-nitrobenzoic acid (7). Reduction of the nitro group followed by derivatization of the so formed anilines 14 gave the N-alkyl-(15a-c), N-acyl-(16a,b and 19), and N-vinyl derivative 20. NMR spectra of (S)-alanine and (S)-proline derived compounds 12, 13, 14-16, 19, and 20 exhibited two sets of signals corresponding to pairs of conformational diastereomers. The free energy barriers of rotation, ΔG(‡)298 = 82-86 kJ mol(-1), were determined by (1)H NMR for 12a, 12d, 12f, and 12g and evaluated by DFT calculations.

Publication Types