Synthesis of Some Medicinal and Biological Active (2E)-2-(5-Substituted 2-thienylmethylene)-4-oxo-4- arylbutanamides and (2E,3Z)-4-hydroxy-4-aryl-2-(5-substituted thien-2-ylmethylene)but-3-enohydrazides
Boshra M Awad, Hanaa A Saad, Ekhlass M Nassar, Eman M Azmy;
Abstract
Solvent-free microwave irradiation of (3E)-5-phenyl-3-(2-thienylmethylene)furan-2(3H)-one 1, (3E)-5-(4-
methylphenyl)-3-(2-thienylmethylene)furan-2(3H)-one 2, and (3E)-3-[(5-methyl-2-thienyl)methylene]-5-
phenylfuran-2(3H)-one 3 with aromatic and aliphatic amines (a-g and i) gave the corresponding (2E)-2-(5-
substituted 2-thienylmethylene)-4-oxo-4-arylbutanamides 4-10, 12, 13-19, 21, 22-28, and 30. However, reaction of
furanones 1-3 with hydrazine hydrate (h) gave (2E,3Z)-4-hydroxy-4-phenyl-2-(thien-2-ylmethylene)but-3-
enohydrazide 11, (2E,3Z)-4-hydroxy-4-(4-methylphenyl)-2-(thien-2-ylmethylene)but-3-enohydrazide 20, and
(2E,3Z)-4-hydroxy-2-[(5-methylthien-2-yl)methylene]-4-phenylbut-3-enohydrazide 29, respectively. Comparison
between microwave-assisted and thermal heating synthesis of compounds 4-30 showed that microwave irradiation
significantly reduces the reaction time with the enhancement of yields and purity. Structural formulas of synthesized
compounds were assigned by their spectral data. Mechanisms of reactions are proposed. Some synthesized products
showed antibacterial and cytotoxic activity.
methylphenyl)-3-(2-thienylmethylene)furan-2(3H)-one 2, and (3E)-3-[(5-methyl-2-thienyl)methylene]-5-
phenylfuran-2(3H)-one 3 with aromatic and aliphatic amines (a-g and i) gave the corresponding (2E)-2-(5-
substituted 2-thienylmethylene)-4-oxo-4-arylbutanamides 4-10, 12, 13-19, 21, 22-28, and 30. However, reaction of
furanones 1-3 with hydrazine hydrate (h) gave (2E,3Z)-4-hydroxy-4-phenyl-2-(thien-2-ylmethylene)but-3-
enohydrazide 11, (2E,3Z)-4-hydroxy-4-(4-methylphenyl)-2-(thien-2-ylmethylene)but-3-enohydrazide 20, and
(2E,3Z)-4-hydroxy-2-[(5-methylthien-2-yl)methylene]-4-phenylbut-3-enohydrazide 29, respectively. Comparison
between microwave-assisted and thermal heating synthesis of compounds 4-30 showed that microwave irradiation
significantly reduces the reaction time with the enhancement of yields and purity. Structural formulas of synthesized
compounds were assigned by their spectral data. Mechanisms of reactions are proposed. Some synthesized products
showed antibacterial and cytotoxic activity.
Other data
Title | Synthesis of Some Medicinal and Biological Active (2E)-2-(5-Substituted 2-thienylmethylene)-4-oxo-4- arylbutanamides and (2E,3Z)-4-hydroxy-4-aryl-2-(5-substituted thien-2-ylmethylene)but-3-enohydrazides | Authors | Boshra M Awad, Hanaa A Saad, Ekhlass M Nassar, Eman M Azmy | Issue Date | 2013 |
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