Chemistry Department, Faculty of Science, Kuwait University, P.O. Box 5969, Safat 13060, Kuwait.
Molecules. 2012 May 25;17(6):6362-85. doi: 10.3390/molecules17066362.
The 4-thiazolidinones 3a-d were used as a key intermediates for the synthesis of 2-arylimino-5-arylidene-4-thiazolidinones derivatives 7a–p via nucleophilic addition reactions with the arylidene malononitrile. Moreover the 4-thiazolidinones 3a and 3c condensed with the DMF-DMA to form the corresponding enamines 8 and 9 depending on the reaction conditions. Otherwise the 4-thiazolidinone 3b reacts regioselectively with DMF-DMA to afford the enaminones 10 and 11, respectively. The latter reacts with many heterocyclic amines affording polyfunctionally substituted fused pyrimidine derivatives 13-18. The enamine 8b was also reacted with the 3-amino-1,2,4-triazole to afford the acyclic product 19, which could not be further cyclized to the corresponding tricyclic system 20. Moreover the 4-thiazolidinone 3c reacted with the benzenediazonium chloride to afford the arylhydrazones 12. The X-ray single crystal technique was employed in this study for structure elucidation and Z/E potential isomerism configuration determination. The X-ray crystallographic analyses of eight products could be obtained, thus establishing with certainty the structures proposed in this work.
4-噻唑烷酮 3a-d 被用作合成 2-芳基亚氨基-5-芳基亚甲基-4-噻唑烷酮衍生物 7a-p 的关键中间体，通过与芳基亚甲基丙二腈的亲核加成反应。此外，4-噻唑烷酮 3a 和 3c 根据反应条件与 DMF-DMA 缩合形成相应的烯胺 8 和 9。否则，4-噻唑烷酮 3b 与 DMF-DMA 反应具有区域选择性，分别得到烯胺酮 10 和 11。后者与许多杂环胺反应得到多官能取代的稠合嘧啶衍生物 13-18。烯胺 8b 也与 3-氨基-1,2,4-三唑反应得到非循环产物 19，其不能进一步环化得到相应的三环体系 20。此外，4-噻唑烷酮 3c 与苯重氮氯化物反应得到芳基腙 12。本研究采用 X 射线单晶技术进行结构阐明和 Z/E 潜在异构体构型确定。可以获得八个产物的 X 射线晶体学分析，从而确定了本工作中提出的结构。
