Gold-Catalyzed Synthesis of 2,5-Disubstituted Oxazoles from Carboxamides and Propynals

被引:19
作者
Xu, Yun [1 ,2 ]
Wang, Qian [1 ]
Wu, Yufeng [1 ]
Zeng, Zhongyi [1 ]
Rudolph, Matthias [1 ]
Hashmi, A. Stephen K. [1 ,3 ]
机构
[1] Heidelberg Univ, Inst Organ Chem, Neuenheimer Feld 270, D-69120 Heidelberg, Germany
[2] China Pharmaceut Univ, Sch Engn, Dept Environm Sci, Nanjing 211198, Jiangsu, Peoples R China
[3] KAU, Fac Sci, Dept Chem, Jeddah 21589, Saudi Arabia
基金
中国国家自然科学基金;
关键词
gold catalysis; gold carbenoids; carboxamides; N-oxides; oxazoles; OXIDATIVE CYCLIZATION; PROPARGYLIC AMIDES; EFFICIENT; ALKYNE; CARBENES; INHIBITORS; ACCESS;
D O I
10.1002/adsc.201801386
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
2,5-Disubstituted oxazoles are synthesized by oxidative gold catalysis. In contrast to a reported procedure that delivers 2,4-disubstituted oxazoles starting from terminal alkynes, a switch in selectivity towards a 2,5-disubstitution is achieved by the use of propynals as starting materials. In the new reaction, the key intermediate is formed by the nucleophilic attack of the carboxamide onto a gold carbenoid, and then condensates with the more electrophilic aldehyde moiety already present in the substrate and not with the ketone that is derived from the oxygen donor. This new cyclization mode introduces a new carbonyl moiety as substituent at the 2,5-disubstituted oxazole, an attractive motive that can be found in bioactive compounds or be used for further derivatizations.
引用
收藏
页码:2309 / 2314
页数:6
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