An Efficient One-Pot, Three-Component Synthesis of 5-Hydrazinoalkylidene Rhodanines from 1,2-Diaza-1,3-dienes

Abstract

A novel three-component synthesis of 5-hydrazinoalkylidene rhodanine derivatives starting from aliphatic primary amines, carbon disulfide, and 1,2-diaza-1,3-dienes is described. The reaction proceeds successfully under both solution and solid-phase conditions.

Multicomponent Reactions for the Synthesis of Heterocycles

“…[43] Favi and co-workers described a new three-component synthesis of 5-hydrazinoalkylidene rhodanine derivatives 26 by starting from aliphatic primary amines, carbon disulfide, and 1,2-diaza-1,3-dienes (Scheme 21; DIPEA = N,N-diisopropylethylamine). [44] The authors optimized the reaction of benzylamine with carbon disulfide and 1,2-diaza-1,3-diene at room temperature in THF without the use of any base. The best yields of the desired product were achieved when the starting components were used in the ratio 1.5:1/3.…”

Synthesis of nitrogen heterocycles from ethyl 3-(6-dibenzothiophen-2-yl-pyridazin-3-ylamino)-3-oxopropanoate

“…Based on the reported observations and in continuation of our research interest for the synthesis of biologically active heterocycles [21][22][23][24], the aim of this study is to design simple route for the synthesis of pyrazoles, triazoles, pyridinones and pyrimidinones derivatives attached to pyridazine moiety.…”

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

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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.

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“…explored as new materials because of their superconducting, optical, and electronic switching properties [17][18][19][20][21][22][23].…”