Russian Journal of Organic Chemistry, volume 37, issue 10, pages 1455-1462
New Fluoroaryl-containing β,β'-Dioxoesters in the Synthesis of Fluorobenzopyran-2(4)-ones
1
Ural Division, Russian Academy of Sciences, Institute of Organic Chemistry, Yekaterinburg, Russia
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Publication type: Journal Article
Publication date: 2001-01-01
Journal:
Russian Journal of Organic Chemistry
Quartile SCImago
Q4
Quartile WOS
Q4
SJR: 0.189
CiteScore: 1.4
Impact factor: 0.8
ISSN: 10704280, 16083393
Organic Chemistry
Abstract
For the first time were obtained ethyl 2-(2-methoxy-3,4,5,6-tetrafluorobenzoyl)-3-oxobutanoate and ethyl 2-pentafluorobenzoyl-3-oxobutanoate and their copper chelates. The compounds were prepared by acylation of ethyl acetoacetate with 2-methoxy-3,4,5,6-tetrafluoro- and pentafluorobenzoyl chlorides. Cyclization of these β,β'-dioxoesters afforded substituted chromones. 2-Methyl-5-methoxy-6,7,8-trifluoro-3-ethoxycarbonylchromone hydrolyzes depending on reaction conditions either to 5-hydroxy-2-methyl-6,7,8-trifluorochromone or to 5-hydroxy-2-methyl-6,7,8-trifluorochromone-3-carboxylic acid. Reaction with morpholine provided 7-substituted product, and with aqueous ammonia as a result of rearrangement forms 3-acetimidoyl-4-hydroxy-5-methoxy-6,7,8-trifluorocoumarin. Hydrolysis of the latter yields 3-acetyl-4-hydroxy-5-methoxy-6,7,8-trifluorocoumarin.
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Kisil’ S., Burgart Y. V., Saloutin V. I. New Fluoroaryl-containing β,β'-Dioxoesters in the Synthesis of Fluorobenzopyran-2(4)-ones // Russian Journal of Organic Chemistry. 2001. Vol. 37. No. 10. pp. 1455-1462.
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Kisil’ S., Burgart Y. V., Saloutin V. I. New Fluoroaryl-containing β,β'-Dioxoesters in the Synthesis of Fluorobenzopyran-2(4)-ones // Russian Journal of Organic Chemistry. 2001. Vol. 37. No. 10. pp. 1455-1462.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1023/a:1013479323203
UR - https://doi.org/10.1023/a:1013479323203
TI - New Fluoroaryl-containing β,β'-Dioxoesters in the Synthesis of Fluorobenzopyran-2(4)-ones
T2 - Russian Journal of Organic Chemistry
AU - Kisil’, S.P
AU - Burgart, Ya. V.
AU - Saloutin, V. I.
PY - 2001
DA - 2001/01/01
PB - Pleiades Publishing
SP - 1455-1462
IS - 10
VL - 37
SN - 1070-4280
SN - 1608-3393
ER -
Cite this
BibTex
Copy
@article{2001_Kisil’,
author = {S.P Kisil’ and Ya. V. Burgart and V. I. Saloutin},
title = {New Fluoroaryl-containing β,β'-Dioxoesters in the Synthesis of Fluorobenzopyran-2(4)-ones},
journal = {Russian Journal of Organic Chemistry},
year = {2001},
volume = {37},
publisher = {Pleiades Publishing},
month = {jan},
url = {https://doi.org/10.1023/a:1013479323203},
number = {10},
pages = {1455--1462},
doi = {10.1023/a:1013479323203}
}
Cite this
MLA
Copy
Kisil’, S.P, et al. “New Fluoroaryl-containing β,β'-Dioxoesters in the Synthesis of Fluorobenzopyran-2(4)-ones.” Russian Journal of Organic Chemistry, vol. 37, no. 10, Jan. 2001, pp. 1455-1462. https://doi.org/10.1023/a:1013479323203.