A facile and efficient one-pot synthesis of 6-amino-2-oxo-4-aryl-4H-1,3-dithiine-5-carbonitrile derivatives in water

Abstract

explored as new materials because of their superconducting, optical, and electronic switching properties [17][18][19][20][21][22][23].The majority of the reactions between carbon disulfide and N-nucleophiles involve addition of carbon disulfide to N-H bonds. The products of these reactions, dithiocarbamate salts, reacts with epoxides [24, 25], 2-chloro-1,3-dicarbonyl compounds [26], chloroacetic acid [27], diethyl 2-chloromalonate [28], ethyl bromopyruvate [29], α-haloketones [30], 3,4-dihydro-2H-pyran [31], electrondeficient alkenes [32], β-nitrostyrene derivatives [33], dibenzoylacetylene [34], quinones [35], and itaconic anhydride [36] that can be transformed into dithiocarbamate derivatives.To the best of our knowledge, there has not been any report on the reaction between carbon disulfide and amines in the presence of arylidenemalononitriles. Herein, we report a one-pot three-component synthesis of 6-amino-2-oxo-4-aryl-4H-1,3-dithiine-5-carbonitriles from amines, carbon disulfide, and arylidenemalononitriles as starting materials. ExperimentalAll chemicals were purchased from Aldrich and Merck with high-grade quality and were used without any purification. All melting points were obtained on a Barnstead Electrothermal 9200 apparatus and are uncorrected. The reactions were monitored by TLC, and all yields refer to isolated products. 1 H and 13 C NMR spectra were recorded in DMSO-d 6 on a Bruker 400 MHz spectrometer. Infrared spectra were recorded on a Bruker FT-IR Equinax-55 spectrophotometer in KBr with absorption in cm −1 . Elemental analyses were performed using a Carlo Erba EA 1108 instrument. All products were characterized by their spectral and physical data.Abstract A one-pot three-component synthesis of 6-amino-2-oxo-4-aryl-4H-1,3-dithiine-5-carbonitriles from amines, carbon disulfide, and arylidenemalononitriles in H 2 O under reflux conditions, in good yields, is described.