Chinese Journal of Organic Chemistry >
Iron-Catalyzed Green Synthesis of 2-Alkenylazaarenes
Received date: 2014-02-05
Revised date: 2014-03-22
Online published: 2014-04-02
Supported by
Project supported by the National Natural Science Foundation of China (No. 21202092) and the Startup Foundation from China Three Gorges University (No. KJ2012B080).
A straightforward and selective synthesis of bioactive trans-2-alkenylazaarenes has been achieved via cheap and nontoxic iron(II) acetate catalyzed addition and dehydration reactions of 2-methylazaarenes and aromatic aldehydes in the presence of catalytic amount of trifluoroacetic acid with water as the only byproduct. The low catalyst loading, convenience, good yield, high selectivity, as well as the broad substrate scope make this protocol very practical. The practical potential was also demonstrated by gram-scale synthesis of (E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde (3v), an intermediate of Singulair.
Key words： alkenylation; nitrogen heterocycles; C-H activation; green chemistry
Liu Sensheng , Jiang Kun , Pi Danwei , Zhou Haifeng , Uozumi Yasuhiro , Zou Kun . Iron-Catalyzed Green Synthesis of 2-Alkenylazaarenes[J]. Chinese Journal of Organic Chemistry, 2014 , 34(7) : 1369 -1375 . DOI: 10.6023/cjoc201402005
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