Cy2NH·HX-Promoted Cyclizations of o-(Alk-1-ynyl)benzoates and (Z)-Alk-2-en-4-ynoate with Copper Halides to Synthesize Isocoumarins and α-Pyrone
Publication type: Journal Article
Publication date: 2007-02-01
scimago Q2
wos Q2
SJR: 0.559
CiteScore: 4.6
Impact factor: 2.3
ISSN: 00397881, 1437210X
Catalysis
Organic Chemistry
Abstract
Cy 2 NH·HX was found to improve the cyclization reactions of o-(alk-1 -ynyl)benzoates and (Z)-alk-2-en-4-ynoate with CuX 2 (X = Cl, Br) to synthesize the corresponding 4-haloisocoumarins and 5-bromo-2-pyrone, respectively. In the presence of two equivalents of CuCl 2 , cyclization of methyl 2-(2-phenylethynyl)benzoate was conducted smoothly to afford the corresponding desired product in 83% yield after 24 hours, whereas the yield was enhanced to 91% in eight hours when 0.1 equivalent of Cy 2 NH·HCl was added. Under the standard reaction conditions, a variety of o-(alk-1 -ynyl)benzoates and (Z)-alk-2-en-4-ynoate underwent the cyclization reaction with CUX 2 to provide the corresponding 4-haloisocoumarins and 5-bromo-2-pyrone, respectively, in moderate to excellent yields.
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Total citations:
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Citations from 2024:
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Liang Y., Li J. Cy2NH·HX-Promoted Cyclizations of o-(Alk-1-ynyl)benzoates and (Z)-Alk-2-en-4-ynoate with Copper Halides to Synthesize Isocoumarins and α-Pyrone // Synthesis. 2007. Vol. 2007. No. 3. pp. 400-406.
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Liang Y., Li J. Cy2NH·HX-Promoted Cyclizations of o-(Alk-1-ynyl)benzoates and (Z)-Alk-2-en-4-ynoate with Copper Halides to Synthesize Isocoumarins and α-Pyrone // Synthesis. 2007. Vol. 2007. No. 3. pp. 400-406.
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TY - JOUR
DO - 10.1055/s-2006-958960
UR - https://doi.org/10.1055/s-2006-958960
TI - Cy2NH·HX-Promoted Cyclizations of o-(Alk-1-ynyl)benzoates and (Z)-Alk-2-en-4-ynoate with Copper Halides to Synthesize Isocoumarins and α-Pyrone
T2 - Synthesis
AU - Liang, Yun
AU - Li, Jinheng
PY - 2007
DA - 2007/02/01
PB - Georg Thieme Verlag KG
SP - 400-406
IS - 3
VL - 2007
SN - 0039-7881
SN - 1437-210X
ER -
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BibTex (up to 50 authors)
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@article{2007_Liang,
author = {Yun Liang and Jinheng Li},
title = {Cy2NH·HX-Promoted Cyclizations of o-(Alk-1-ynyl)benzoates and (Z)-Alk-2-en-4-ynoate with Copper Halides to Synthesize Isocoumarins and α-Pyrone},
journal = {Synthesis},
year = {2007},
volume = {2007},
publisher = {Georg Thieme Verlag KG},
month = {feb},
url = {https://doi.org/10.1055/s-2006-958960},
number = {3},
pages = {400--406},
doi = {10.1055/s-2006-958960}
}
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MLA
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Liang, Yun, and Jinheng Li. “Cy2NH·HX-Promoted Cyclizations of o-(Alk-1-ynyl)benzoates and (Z)-Alk-2-en-4-ynoate with Copper Halides to Synthesize Isocoumarins and α-Pyrone.” Synthesis, vol. 2007, no. 3, Feb. 2007, pp. 400-406. https://doi.org/10.1055/s-2006-958960.