Abstract
Herein, we describe a practical and efficient method for the C3-alkylation of 4-hydroxycoumarin by sonication under 'on water' conditions and mild temperatures using various substituted β-nitrostyrenes. In addition, we report on the development of a convenient process for the regioselective synthesis of angular hydroxyiminodihydrofuroquinolinone catalyzed by base. 4-Hydroxycoumarin and 4-hydroxy-1-methylquinolin-2(1H)-one reacted smoothly with various nitroolefins to furnish C3-nitroalkylated hydroxycoumarin derivatives (by sonication and 'on water' conditions) and hydroxyiminodihydrofuroquinolinone derivatives (ambient condition) as a mixture of Z (minor) and E (major) isomers, respectively. The mild reaction conditions employed, ease of isolation of the products and excellent yields constitute important features of the methodology.
| Original language | English |
|---|---|
| Pages (from-to) | 2870-2877 |
| Number of pages | 8 |
| Journal | Tetrahedron |
| Volume | 67 |
| Issue number | 16 |
| DOIs | |
| Publication status | Published - 2011 Apr 22 |
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ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
Cite this
Synthesis of C3-nitroalkylated-4-hydroxycoumarin and hydroxyiminodihydrofuroquinolinone derivatives via the Michael addition of cyclic 1,3-dicarbonyl compounds to β-nitrostyrenes. / Barange, Deepak Kumar; Kavala, Veerababurao; Kuo, Chun Wei; Lei, Po Min; Yao, Ching Fa.
In: Tetrahedron, Vol. 67, No. 16, 22.04.2011, p. 2870-2877.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Synthesis of C3-nitroalkylated-4-hydroxycoumarin and hydroxyiminodihydrofuroquinolinone derivatives via the Michael addition of cyclic 1,3-dicarbonyl compounds to β-nitrostyrenes
AU - Barange, Deepak Kumar
AU - Kavala, Veerababurao
AU - Kuo, Chun Wei
AU - Lei, Po Min
AU - Yao, Ching Fa
PY - 2011/4/22
Y1 - 2011/4/22
N2 - Herein, we describe a practical and efficient method for the C3-alkylation of 4-hydroxycoumarin by sonication under 'on water' conditions and mild temperatures using various substituted β-nitrostyrenes. In addition, we report on the development of a convenient process for the regioselective synthesis of angular hydroxyiminodihydrofuroquinolinone catalyzed by base. 4-Hydroxycoumarin and 4-hydroxy-1-methylquinolin-2(1H)-one reacted smoothly with various nitroolefins to furnish C3-nitroalkylated hydroxycoumarin derivatives (by sonication and 'on water' conditions) and hydroxyiminodihydrofuroquinolinone derivatives (ambient condition) as a mixture of Z (minor) and E (major) isomers, respectively. The mild reaction conditions employed, ease of isolation of the products and excellent yields constitute important features of the methodology.
AB - Herein, we describe a practical and efficient method for the C3-alkylation of 4-hydroxycoumarin by sonication under 'on water' conditions and mild temperatures using various substituted β-nitrostyrenes. In addition, we report on the development of a convenient process for the regioselective synthesis of angular hydroxyiminodihydrofuroquinolinone catalyzed by base. 4-Hydroxycoumarin and 4-hydroxy-1-methylquinolin-2(1H)-one reacted smoothly with various nitroolefins to furnish C3-nitroalkylated hydroxycoumarin derivatives (by sonication and 'on water' conditions) and hydroxyiminodihydrofuroquinolinone derivatives (ambient condition) as a mixture of Z (minor) and E (major) isomers, respectively. The mild reaction conditions employed, ease of isolation of the products and excellent yields constitute important features of the methodology.
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U2 - 10.1016/j.tet.2011.02.062
DO - 10.1016/j.tet.2011.02.062
M3 - Article
AN - SCOPUS:79953170500
VL - 67
SP - 2870
EP - 2877
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 16
ER -