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Intramolecular Schmidt Reaction of Acyl Chlorides with Alkyl Azides: Rapid Access to Fused Polycyclic Nitrogen-Containing Heterocycles via a Multistep One-Pot Transformation

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posted on 16.11.2012, 00:00 by Peiming Gu, Xiao-Yan Kang, Jian Sun, Bao-Juan Wang, Ming Yi, Xue-Qiang Li, Ping Xue, Rui Li
The first intramolecular Schmidt reaction of acyl chlorides with alkyl azides has been developed. In this one-pot conversion, an ω-azido hydrocinnamic acid is converted to a tricyclic lactam. The most important feature of the process is the efficiency in bond formation (one bond broken and three new bonds created) and ring construction (two new rings formed).