Abstract
The reactions of dialkyl acetylenedicarboxylates with various 2-oxo-acenaphthoquinylidene- and 4-acetyl[2.2]paracyclophanylidene-thiosemicarbazones were investigated. Using simple experimental procedures, 1,3-Thiazolidin-4-ones derived from acenaphthequinone or [2.2]paracyclophane were obtained as major products in good yields. In the case of allyl derivative of acenaphthoquinylidene-thiosemicarbazones, a complex structure of tetramethyl 5-(2-(((Z,E)-N-allyl-N′-(2-oxoacenaphthylen-1(2H)-ylidene)carbamohydrazonoyl)thio)-1,2,3-tris-(methoxycarbonyl)-cyclopropyl)-4-methoxy-7-oxabicyclo[2.2.1]hepta-2,5-diene-1,2,3,6-tetracarboxylate was formed. Single crystal X-ray analysis was used as an efficient tool to confirm the structure of the synthesized compounds as well as different spectroscopic data (1H-NMR, 13C-NMR, 2D-NMR, mass spectrometry and elemental analysis). The mechanism of the obtained products was discussed.
Highlights
Of interest due to their high biological activities, 1,3-Thiazolidin-4-one derivatives are very important core structures of many heterocyclic compounds
Various synthetic routes were used for the synthesis of different thiazolidinones from several thiosemicarbazides and thiocarbohydrazides by using different reagents, and their biological evaluation was discussed [8,9]
Thiosemicarbazones were used as a starting material for the synthesis of different heterocyclic compounds, i.e., naphtho-thiazole and naphtho-thiadiazepines [10], 4-thiazolidinone derivatives [11,12], 1,3,4-thiadiazoles [13] which possess high biological activities, e.g., anticancer [14], antioxidants [15], antifungal [16], and antibacterial [17]
Summary
Of interest due to their high biological activities, 1,3-Thiazolidin-4-one derivatives are very important core structures of many heterocyclic compounds. Thiosemicarbazones were used as a starting material for the synthesis of different heterocyclic compounds, i.e., naphtho-thiazole and naphtho-thiadiazepines [10], 4-thiazolidinone derivatives [11,12], 1,3,4-thiadiazoles [13] which possess high biological activities, e.g., anticancer [14], antioxidants [15], antifungal [16], and antibacterial [17]. Acenaphthequinone (acenaphthylene-1,2-dione) is a quinone derivative, widely used as significant starting material for the synthesis of various heterocycles, and as a key intermediate in organic synthesis for different reactions and pharmaceutical applications [18,19,20,21]. We aim here to synthesize various thiazolidinone derivatives of both acenaphthequinone and [2.2]paracyclophane
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