Reactions of 2-bromopropanamides with conjugated bases of representative β-dicarbonyl compounds. Synthesis of 2,5-dioxopyrrolidines and oxazolidine-4-ones
1
Dipartimento di Scienze Farmaceutiche, Via Fossato di Mortara 19, I-44100 Ferrara, Italy
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Publication type: Journal Article
Publication date: 2003-05-12
scimago Q3
wos Q3
SJR: 0.334
CiteScore: 3.2
Impact factor: 1.5
ISSN: 00404039, 18733581
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
Reactions of 2-bromopropanamides with potassium enolates of representative β-dicarbonyl compounds provide, in high yields, open and heterocyclic compounds through a CC or CO alkylation reaction. Whereas C-alkylation products form in all conditions tested under relevant diastereoselectivity, O-alkylation takes place only in the presence of silver promoters, and shows partial diastereoselectivity.
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Marchetti P. Reactions of 2-bromopropanamides with conjugated bases of representative β-dicarbonyl compounds. Synthesis of 2,5-dioxopyrrolidines and oxazolidine-4-ones // Tetrahedron Letters. 2003. Vol. 44. No. 21. pp. 4121-4123.
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Marchetti P. Reactions of 2-bromopropanamides with conjugated bases of representative β-dicarbonyl compounds. Synthesis of 2,5-dioxopyrrolidines and oxazolidine-4-ones // Tetrahedron Letters. 2003. Vol. 44. No. 21. pp. 4121-4123.
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TY - JOUR
DO - 10.1016/s0040-4039(03)00853-0
UR - https://doi.org/10.1016/s0040-4039(03)00853-0
TI - Reactions of 2-bromopropanamides with conjugated bases of representative β-dicarbonyl compounds. Synthesis of 2,5-dioxopyrrolidines and oxazolidine-4-ones
T2 - Tetrahedron Letters
AU - Marchetti, Paolo
PY - 2003
DA - 2003/05/12
PB - Elsevier
SP - 4121-4123
IS - 21
VL - 44
SN - 0040-4039
SN - 1873-3581
ER -
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BibTex (up to 50 authors)
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@article{2003_Marchetti,
author = {Paolo Marchetti},
title = {Reactions of 2-bromopropanamides with conjugated bases of representative β-dicarbonyl compounds. Synthesis of 2,5-dioxopyrrolidines and oxazolidine-4-ones},
journal = {Tetrahedron Letters},
year = {2003},
volume = {44},
publisher = {Elsevier},
month = {may},
url = {https://doi.org/10.1016/s0040-4039(03)00853-0},
number = {21},
pages = {4121--4123},
doi = {10.1016/s0040-4039(03)00853-0}
}
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MLA
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Marchetti, Paolo. “Reactions of 2-bromopropanamides with conjugated bases of representative β-dicarbonyl compounds. Synthesis of 2,5-dioxopyrrolidines and oxazolidine-4-ones.” Tetrahedron Letters, vol. 44, no. 21, May. 2003, pp. 4121-4123. https://doi.org/10.1016/s0040-4039(03)00853-0.