کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5221242 1383415 2011 8 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Synthesis of C3-nitroalkylated-4-hydroxycoumarin and hydroxyiminodihydrofuroquinolinone derivatives via the Michael addition of cyclic 1,3-dicarbonyl compounds to β-nitrostyrenes
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Synthesis of C3-nitroalkylated-4-hydroxycoumarin and hydroxyiminodihydrofuroquinolinone derivatives via the Michael addition of cyclic 1,3-dicarbonyl compounds to β-nitrostyrenes
چکیده انگلیسی

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.

4-Hydroxycoumarin and 4-hydroxy-1-methylquinolin-2(1H)-one reacted smoothly with various β-nitrostyrenes to furnish C3-nitroalkylated 4-hydroxycoumarin derivatives by sonication under ‘on water’ conditions and hydroxyiminodihydrofuroquinolinone derivatives at ambient condition as a mixture of Z (minor) and E (major) isomers, respectively. The mild reaction conditions employed, allowed the products to be easily isolated in excellent yields, are among the important features of the methodology. Figure optionsDownload as PowerPoint slide

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 67, Issue 16, 22 April 2011, Pages 2870–2877