Synthesis of 2-Substituted-5-halo-2,3-dihydro-4(H)-pyrimidin-4-ones and Their Derivatization Utilizing the Sonogashira Coupling Reaction in the Enantioselective Synthesis of α-Substituted β-Amino Acids
Тип публикации: Journal Article
Дата публикации: 2007-05-25
scimago Q2
wos Q1
БС1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
17523668
Organic Chemistry
Краткое описание
A convenient, one-pot procedure for the synthesis of 1-benzoyl-2(S)-substituted-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-ones by tandem decarboxylation/beta-iodination of the corresponding 6-carboxy-perhydropyrimidin-4-ones was developed. In addition, several 1-benzoyl-2(S)-substituted-5-bromo-2,3-dihydro-4(H)-pyrimidin-4-ones were readily prepared by bromination of 1-benzoyl-2(S)-substituted-2,3-dihydro-4(H)-pyrimidin-4-ones. Subsequently, Sonogashira coupling of the halogenated heterocyclic enones with various terminal alkynes produced 1-benzoyl-2(S)-isopropyl-5-alkynyl-2,3-dihydro-4(H)-pyrimidin-4-ones in good yields. Hydrogenation of the unsaturated C-C moieties in the Sonogashira products followed by acid hydrolysis afforded highly enantioenriched alpha-substituted beta-amino acids.
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Díaz-Sánchez B. R. et al. Synthesis of 2-Substituted-5-halo-2,3-dihydro-4(H)-pyrimidin-4-ones and Their Derivatization Utilizing the Sonogashira Coupling Reaction in the Enantioselective Synthesis of α-Substituted β-Amino Acids // Journal of Organic Chemistry. 2007. Vol. 72. No. 13. pp. 4822-4825.
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Díaz-Sánchez B. R., Iglesias Arteaga M. A., Melgar-Fernández R., Juaristi E. Synthesis of 2-Substituted-5-halo-2,3-dihydro-4(H)-pyrimidin-4-ones and Their Derivatization Utilizing the Sonogashira Coupling Reaction in the Enantioselective Synthesis of α-Substituted β-Amino Acids // Journal of Organic Chemistry. 2007. Vol. 72. No. 13. pp. 4822-4825.
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TY - JOUR
DO - 10.1021/jo0705115
UR - https://doi.org/10.1021/jo0705115
TI - Synthesis of 2-Substituted-5-halo-2,3-dihydro-4(H)-pyrimidin-4-ones and Their Derivatization Utilizing the Sonogashira Coupling Reaction in the Enantioselective Synthesis of α-Substituted β-Amino Acids
T2 - Journal of Organic Chemistry
AU - Díaz-Sánchez, Blanca R.
AU - Iglesias Arteaga, Martín A
AU - Melgar-Fernández, Roberto
AU - Juaristi, Eusebio
PY - 2007
DA - 2007/05/25
PB - American Chemical Society (ACS)
SP - 4822-4825
IS - 13
VL - 72
PMID - 17523668
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2007_Díaz-Sánchez,
author = {Blanca R. Díaz-Sánchez and Martín A Iglesias Arteaga and Roberto Melgar-Fernández and Eusebio Juaristi},
title = {Synthesis of 2-Substituted-5-halo-2,3-dihydro-4(H)-pyrimidin-4-ones and Their Derivatization Utilizing the Sonogashira Coupling Reaction in the Enantioselective Synthesis of α-Substituted β-Amino Acids},
journal = {Journal of Organic Chemistry},
year = {2007},
volume = {72},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://doi.org/10.1021/jo0705115},
number = {13},
pages = {4822--4825},
doi = {10.1021/jo0705115}
}
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MLA
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Díaz-Sánchez, Blanca R., et al. “Synthesis of 2-Substituted-5-halo-2,3-dihydro-4(H)-pyrimidin-4-ones and Their Derivatization Utilizing the Sonogashira Coupling Reaction in the Enantioselective Synthesis of α-Substituted β-Amino Acids.” Journal of Organic Chemistry, vol. 72, no. 13, May. 2007, pp. 4822-4825. https://doi.org/10.1021/jo0705115.