Abstract
The solid-solid reactions of thiosemicarbazide with 4-formylantipyrine, 2-acetylpyrrole and camphor were performed to afford the thiosemicarbazones 1–3 which underwent hetero-cyclization with phenacyl bromide to furnish the corresponding thiazole derivatives 4–6. The yields of the reactions are quantitative in all cases and the products do not require further purification. A series of 5-arylazo-2-(substituted ylidene-hydrazinyl)-thiazole dyes 7–9 was then prepared by diazo coupling of thiazole derivatives 4–6 with several diazonium chlorides. The synthesized dyes were applied as disperse dyes for dyeing polyester fabric. The dyed fabrics exhibit good washing, perspiration, sublimation and light fastness properties, with little variation in their moderate to good rubbing fastness.
Highlights
Stoichiometric solid-solid reactions are most versatile for the waste-free production of a single product, while melt reactions more frequently have the risk of side reactions, even if these are considerably better than solution reactions
Thiosemicarbazones are a class of interesting compounds presenting a wide range of pharmacological applications as antitumor, antimicrobial and antiviral agents [3]. α-(N)-Heterocyclic thiosemicarbazones have been extensively investigated by many authors [4,5,6,7,8,9]
This proposal is in agreement with the observed results (Table 1) which demonstrate that the presence of a methyl group in the synthesized dyes causes a decrease of light fastness to 3–4
Summary
Stoichiometric solid-solid reactions are most versatile for the waste-free production of a single product, while melt reactions more frequently have the risk of side reactions, even if these are considerably better than solution reactions. Solvent-free reactions have been reviewed without emphasis of waste-free processes [1]. More than 1000 waste-free quantitative syntheses in organic solid-state chemistry are already known and have been reported in a review article that covers more than 25 reaction types [2]. Thiosemicarbazones are a class of interesting compounds presenting a wide range of pharmacological applications as antitumor, antimicrobial and antiviral agents [3]. Α-(N)-Heterocyclic thiosemicarbazones have been extensively investigated by many authors [4,5,6,7,8,9] Thiosemicarbazones are a class of interesting compounds presenting a wide range of pharmacological applications as antitumor, antimicrobial and antiviral agents [3]. α-(N)-Heterocyclic thiosemicarbazones have been extensively investigated by many authors [4,5,6,7,8,9]
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