色酮(苯并噻喃-4-酮)及其衍生物，是对天然色酮类化合物的1位进行化学修饰而得到的全合成化合物，具有广谱高效的抗真菌活性，是目前研究开发新型抗真菌医药和农药重要的先导结构之一。乙烯基砜作为活泼的离去基团广泛应用于活性染料的亲核取代反应中。本课题将在硫色酮2位引入砜官能团而构建基于硫色酮结构上的乙烯砜官能团，利用乙烯砜的高反应活性进行硫色酮2位取代反应的合成研究并对合成化合物进行表征。

An aryne precursor with a potential to perform domino aryne chemistry was proposed and synthesized. The reaction of this reagent with benzothioa-mide derivatives could afford 2,4-disubstituted benzothia-zole with sequential incorporation of C#8722;S, C#8722;N, and C#8722; C bonds on the consecutive three positions of the aryne precursor.

Arynes are among the most reactive organic species and have been broadly employed in numerous organic syntheses.1 In particular, the success of Kobayashi reagents,o-trimethylsilyl-phenyl triflates, in recent aryne chemistry is primarily attributed to their convenient and mild aryne generation conditions. Because of the formal triple bond character of arynes, however, normally only 1,2-disubstituted aromatics are attainable via aryne intermediates. The preparation of 1,2,3-trisubstituted benzenes, the structure of which prevails in vast groups of organic compounds, are still beyond the boundary of standard aryne chemistry and have yet to be well-documented. Aryne precursors that can assemble three consecutive functional groups on a benzene ring in ”one-pot” fashion, are compatible with various reagents and functional groups, and can perform versatile transformations would largely expand the realm of current aryne

Chemistry.

series of 2,4-disubstituted benzothiazoles is prepared from aryne precursor TPBT 1, whose conversion involves a domino aryne mechanism. By varying the carbonyl groups, either 2-substituted or 2,4-disubstituted benzothiazoles were obtained. A sequential formation of C#8722;S, C#8722;N, and C#8722;C bonds on the 1,2,3-positions of the TPBT 1 benzene ring was achieved. This method is versatile, and the 2,4-disubstituted benzothiazole product could be further converted to other derivatives.

色酮(chromone)又称苯并-γ-吡喃酮，2位或3位有苯基取代的色酮是一类重要植物成分的母核。2-苯基色酮称为黄酮(flavone)，3-苯基色酮称为异黄酮(isofl- avone)，含有这类母核的植物成分通称为黄酮类化合物。例如中药黄芩中含有的黄芩苷(baicalin)，就是其抗真菌活性的有效成分。构效关系研究表明，对色酮2位、3位及4位进行结构修饰，对其抗真菌活性有较大的影响。活性研究表明，无论是天然存在的还是合成得到的色酮类化合物，具有抗过敏、抗菌、抗癌、抗病毒、降血压血脂等广泛生理活性，尤其作为抗真菌药物，目前研究较为活跃，已成为抗真菌药物研发的热点之一。色酮类的化学结构如下图所示:

构效关系表明，色酮母核2位或3位具有取代基是产生抗真菌药效必不可少的部分。黄酮和异黄酮的2位或3位苯环上的2至6位的取代，对色酮抗真菌活性有影响，可以在一定程度上提高其抗真菌活性。在色酮母核2位或3位引入含硫杂环或含氮杂环基团，如咪唑基、三氮唑等基团，对色酮类化合物抗真菌活性有较大的影响，可以显著提高其抗真菌活性。对色酮4位进行杂原子取代修饰，对色酮抗真菌活性具有一定程度的影响。在色酮2位、3位或4位有取 代基的情况下，色酮母核5至8位具有卤素取代，尤其是6位和7位具有卤原子取代情况下，可以提高色酮类化合物的抗真菌活性。

硫色酮及其衍生物，具有与色酮相似的苯并-γ-硫吡喃结构，高脂溶性低水溶性。活性研究表明，硫色酮类化合物具有明显的抗真菌活，目前文献报道的硫色酮类化合物，多以合成得到为主。早在1984年，Nakazu Mi等人就在文献中指出，2位为苯环取代时(10a)，体外具有抗毛癣菌活性(MIC为0.195μg/mL)，10b~10d的MIC为0.00488μg/mL~6.25μg/mL，抗真菌活性较为显著。目前硫色酮类化合物，主要集中在合成方法及结构修饰方面。