Solid-Phase Synthesis of Isocoumarins: A Traceless Halocyclization Approach
Marine Peuchmaur
1
,
Vincent Lisowski
1
,
Céline Gandreuil
1
,
Ludovic Maillard
1
,
JEAN MARTINEZ
1
,
Jean-François Hernandez
1
1
Institut des Biomolécules Max-Mousseron, UMR 5247, CNRS, Universités Montpellier I et II, UFR des Sciences Pharmaceutiques et Biologiques, 15 Avenue Charles Flahault, 34093 Montpellier Cedex 5, France
|
Publication type: Journal Article
Publication date: 2009-05-13
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
19438216
Organic Chemistry
Abstract
A straightforward and traceless solid-phase methodology was developed for the synthesis of isocoumarins. This two-step process involves a Sonogashira cross-coupling reaction between polymer-bound 2-bromobenzoates and terminal alkynes, followed by an electrophile-induced halocyclization of the resulting 2-(alk-1-ynyl)benzoates through activation of the triple bond with the subsequent release of the 3-substituted 4-haloisocoumarins. This polymer-bound parallel synthetic approach allowed us to achieve large diversity in good to excellent yields and purities.
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Total citations:
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Citations from 2024:
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(1.67%)
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GOST
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Peuchmaur M. et al. Solid-Phase Synthesis of Isocoumarins: A Traceless Halocyclization Approach // Journal of Organic Chemistry. 2009. Vol. 74. No. 11. pp. 4158-4165.
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Peuchmaur M., Lisowski V., Gandreuil C., Maillard L., MARTINEZ J., Hernandez J. Solid-Phase Synthesis of Isocoumarins: A Traceless Halocyclization Approach // Journal of Organic Chemistry. 2009. Vol. 74. No. 11. pp. 4158-4165.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/jo900281a
UR - https://doi.org/10.1021/jo900281a
TI - Solid-Phase Synthesis of Isocoumarins: A Traceless Halocyclization Approach
T2 - Journal of Organic Chemistry
AU - Peuchmaur, Marine
AU - Lisowski, Vincent
AU - Gandreuil, Céline
AU - Maillard, Ludovic
AU - MARTINEZ, JEAN
AU - Hernandez, Jean-François
PY - 2009
DA - 2009/05/13
PB - American Chemical Society (ACS)
SP - 4158-4165
IS - 11
VL - 74
PMID - 19438216
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
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@article{2009_Peuchmaur,
author = {Marine Peuchmaur and Vincent Lisowski and Céline Gandreuil and Ludovic Maillard and JEAN MARTINEZ and Jean-François Hernandez},
title = {Solid-Phase Synthesis of Isocoumarins: A Traceless Halocyclization Approach},
journal = {Journal of Organic Chemistry},
year = {2009},
volume = {74},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://doi.org/10.1021/jo900281a},
number = {11},
pages = {4158--4165},
doi = {10.1021/jo900281a}
}
Cite this
MLA
Copy
Peuchmaur, Marine, et al. “Solid-Phase Synthesis of Isocoumarins: A Traceless Halocyclization Approach.” Journal of Organic Chemistry, vol. 74, no. 11, May. 2009, pp. 4158-4165. https://doi.org/10.1021/jo900281a.