A Practical Access to Novel 2‐Amino‐5‐arylidene‐1,3‐thiazol‐4(5H)‐ones via Sulfur/Nitrogen Displacement under Solvent‐Free Microwave Irradiation.

Abstract

A Practical Access to Novel 2-Amino-5-arylidene-1,3-thiazol-4(5H)-ones via Sulfur/Nitrogen Displacement under Solvent-Free Microwave Irradiation. -Knoevenagel condensation of rhodanines with aldimines and subsequent sulfur/nitrogen displacement on the resulting (5Z)-5-arylidene rhodanines offers a simple synthesis of the title compounds which represent important scaffolds in drug discovery. -(BOURAHLA, K.; DERDOUR, A.; RAHMOUNI, M.; CARREAUX, F.; BAZUREAU*, J. P.; Tetrahedron Lett. 48 (2007) 33, 5785-5789; Lab. Sci. Chim. Rennes, Univ. Rennes, F-35042 Rennes, Fr.; Eng.) -Mais 48-119

Synthesis of New N,N'-Bis(5-arylidene-4-oxo-4,5-dihydrothiazolin-2-yl)piperazine Derivatives Under Microwave Irradiation and Preliminary Biological Evaluation

“…Transformation of 5-arylidene rhodanine 3 into 2-amino-5-arylidene-5 H -thiazol-4-one after addition of a primary amine [15] usually involves activation of the C=S bond of rhodanine via the thioether intermediate that subsequently undergoes a thioalkyl/nitrogen displacement. In order to be able to carry out such sulfur/nitrogen displacement in a faster and more efficient way – avoiding the preparation of the thioether intermediate – we examined the influence of microwave irradiation on the reaction between compound 3 and the symmetric diamino linkers 4a,b .…”

Synthesis of 5-arylidene-3-methylrhodanines catalyzed by 1-butyl-3-methylimidazolium chloride in water under microwave irradiation condition

“…Rhodanine derivatives have showed a wide range of biological activities which include anticonvulsant, antibacterial, antiviral and antidiabetic effects [1]. These have also been reported as Hepatitis C virus (HCV) protease inhibitors [2] and used as inhibitors of uridine diphospho-N-acetylmuramate/L-alanine ligase [3].…”

Green Chemical Synthesis and Analgesic Activity of Fluorinated Thiazolidinone, Pyrazolidinone, and Dioxanedione Derivatives

“…Knoevenagel condensation is also reported under microwave irradiation for the synthesis of 5arylidene-4-thiazolidinones [41]. These derivatives are also synthesized using tetrabutylammonium bromide (TBAB) as a phase transfer catalyst in water under microwave irradiation [42]. However, in spite of their utility, some methods suffer from disadvantages like long reaction times, low yields, chemical hazards, and environmental pollution.…”