1,3-Dipolar cycloaddition of imidate ylides on imino-alcohols: Synthesis of new imidazolones using solvent free conditions
Jean Michel Lerestif
1
,
Jacques Perrocheau
1
,
François Tonnard()
2
,
Jean Pierre Bazureau
1
,
Jack Hamelin
1
1
Groupe de Recherches de Physico‐Chimie Structurale 3 associé au CNRS, Campus de Beaulieu, 35042 Rennes Cédex, France
|
2
Groupe Matière Condensée et Matériaux associé au CNRS, Campus de Beaulieu, 35042 - Rennes Cédex, France.
|
Publication type: Journal Article
Publication date: 1995-06-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
Imidates derived from α-amino esters as potential azomethine ylides, undergo 1,3-dipolar cycloaddition with imino-alcohols, in tautomeric equilibrium with 1,3-oxazolidines, without solvent at 70°C or under microwave irradiation. This reaction leads to a wide range of novel polyfunctionalized 4-yliden-2-imidazolin-5-ones in good yields with short reaction times. The reactivity of these imidates derived from α-amino esters with imino-alcohols is rationalized from the energy of the Frontier Molecular Orbitals (FMO) determined by semi-empirical PM3 calculations: the reaction is controlled by the interaction HOMO (1,3-dipole) - LUMO (dipolarophile) and the second order pertubation energy calculations are in agreement with the experimental reaction orientation.
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Total citations:
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Citations from 2025:
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(2.33%)
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GOST
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Lerestif J. M. et al. 1,3-Dipolar cycloaddition of imidate ylides on imino-alcohols: Synthesis of new imidazolones using solvent free conditions // Tetrahedron. 1995. Vol. 51. No. 24. pp. 6757-6774.
GOST all authors (up to 50)
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Lerestif J. M., Perrocheau J., Tonnard() F., Bazureau J. P., Hamelin J. 1,3-Dipolar cycloaddition of imidate ylides on imino-alcohols: Synthesis of new imidazolones using solvent free conditions // Tetrahedron. 1995. Vol. 51. No. 24. pp. 6757-6774.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1016/0040-4020(95)00321-x
UR - https://doi.org/10.1016/0040-4020(95)00321-x
TI - 1,3-Dipolar cycloaddition of imidate ylides on imino-alcohols: Synthesis of new imidazolones using solvent free conditions
T2 - Tetrahedron
AU - Lerestif, Jean Michel
AU - Perrocheau, Jacques
AU - Tonnard(), François
AU - Bazureau, Jean Pierre
AU - Hamelin, Jack
PY - 1995
DA - 1995/06/01
PB - Elsevier
SP - 6757-6774
IS - 24
VL - 51
SN - 0040-4020
SN - 1464-5416
ER -
Cite this
BibTex (up to 50 authors)
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@article{1995_Lerestif,
author = {Jean Michel Lerestif and Jacques Perrocheau and François Tonnard() and Jean Pierre Bazureau and Jack Hamelin},
title = {1,3-Dipolar cycloaddition of imidate ylides on imino-alcohols: Synthesis of new imidazolones using solvent free conditions},
journal = {Tetrahedron},
year = {1995},
volume = {51},
publisher = {Elsevier},
month = {jun},
url = {https://doi.org/10.1016/0040-4020(95)00321-x},
number = {24},
pages = {6757--6774},
doi = {10.1016/0040-4020(95)00321-x}
}
Cite this
MLA
Copy
Lerestif, Jean Michel, et al. “1,3-Dipolar cycloaddition of imidate ylides on imino-alcohols: Synthesis of new imidazolones using solvent free conditions.” Tetrahedron, vol. 51, no. 24, Jun. 1995, pp. 6757-6774. https://doi.org/10.1016/0040-4020(95)00321-x.