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从天然产物中寻找具有药用价值的骨架分子一直是新药寻找的重要途径。通过对具有生物活性的天然产物的分离,结构测定和改造,以及对它们的构效关系进行研究,是促进生物学和药物学飞速发展的强有力的推动力。另外,利用高效有机合成方法和组合化学技术能在相对短的时间内有系统地提供一定量的,结构类似的天然产物类似物。 课题组基于炔基化合物串联环化构建几类杂环化合物:1. 发展了钯催化下的2-烯基环丙烷溴代芳烃与2-炔基苯酚的串联反应,构建了氧杂四并茚环类化合物;2. 实现了银催化的邻炔基苯甲醛肟和邻炔基苯乙烯基环丙烷的反应,合成了系列1-(1-二氢异苯并呋喃环丙基)异喹啉衍生物;3. 发展了溴化铜催化下的N-(2-碘代芳基)炔基亚胺与异氰基乙酸酯的反应,得到了三氟甲基取代的吡咯并[3,2-c]喹啉类化合物。,同时,利用二氧化硫插入策略合成磺酰化合物:反应使用DABCO.(SO2)2作为二氧化硫替代物。实验中发现芳基重氮盐与DABCO.(SO2)2可以在无需金属催化剂和添加剂的条件下,原位产生芳基磺酰基自由基。芳基自由基可以参与多种转化,实现了多种磺酰胺、砜以及砜基取代的杂环化合物的合成。 课题组基于炔烃化合物串联环化反应,成功地实现了几类具有优势骨架的杂环化合物的合成,同时实现了具有磺酰片段的有机分子的构建的新方法,特别是在具有生物活性的类天然小分子化合物的合成中就显得非常重要及有意义,并且这也符合当今社会的可持续发展战略。 [1] Guanyinsheng Qiu, Qiuping Ding and Jie Wu*.Recent advances in isocyanide insertion chemistry. Chem. Soc. Rev. 2013, 42(12): 5257-5269. [2] Danqing Zheng, Yuanyuan An, Zhen Hua Li and Jie Wu* .Metal‐Free Aminosulfonylation of Aryldiazonium Tetrafluoroborates with DABCO?(SO2)2 and Hydrazines. Angew. Chem., Int. Ed. 2014, 53(9): 2451-2454。 [3] Yong Luo, Xiaolin Pan, Xingxin Yu* Jie Wu* Double carbometallation of alkynes: an efficient strategy for the construction of polycycles. Chem. Soc. Rev.2014,43(3): 834-846。 [4] Jie Sheng, Congbin Fan, Yechun Ding, Xiaona Fan* and Jie Wu*. A silver(l) triflate-catalyzed reaction of 1-((cyclopropylidenemethyl)-2-alkynyl)arene with 2-alkynylbenzaldoxime. Chem. Commun, 2014,50:4188-4191。 [5] Xiaolin Pan, Yong Luo, Yechun Ding, Xiaona Fan*, and Jie Wu. Assembly of Indeno [1,2-c]chromenes via a Palladium-Catalyzed Reaction of 1-Bromo-2-(cyclopropylidenemethyl) benzene with 2-Alkynylphenol. Advanced Synthesis & Catalysis, 2014, 356(5):1072 - 1078. [6] Xia Liu, Wei Li, Danqing Zheng, Xiaona Fan* and Jie Wu*. Synthesis of sulfones via a reaction of aryldiazonium tetrafluoroborates, sulfur dioxide, and aryliodoniums .Tetrahedron,2015, 71,3359-3362。 [7] Danqing, Zheng,Tong Liu,Xia Liu, Xiaona Fan* and Jie Wu*. Route for the Generation of Trifluoromethyl-Substituted Pyrrplo[3,2-c]quinolines. J. Org. Chem. 2016, 81, 9428-9432. [8] Runyu Mao, Zheng Yuan, Rui Zhang, Yechun Ding, Xiaona Fan* and Jie Wu*.A copper(II)-catalyzed three-component reaction of aryldiazonium tetrafluoroborates, sulfur dioxide, with alkenes. Org. Chem. Front. 2016, 3, 1498-1502. [9] Danqing Zheng, Jiyao Yu, Jie Wu*.Generation of sulfonyl radicals from aryldiazonium tetrafluoroborates and sulfur dioxide: the synthesis of 3‐sulfonated coumarins. Angew. Chem., Int. Ed. 2016, 55(39): 11925-11929. [10] Tianshuo Liu, Danqing Zheng,Yechun Ding, Xiaona Fan* and Jie Wu* .Synthesis of b-Keto Sulfones by a Catalyst-Free Reaction of Aryldiazonium Tetrafluoroborates, Sulfur Dioxide, and Silyl Enol Ethers . Chem. Asian J. 2017, 12, 465 - 469