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铟催化炔烃的分子内羟胺化反应:通过后转化反应合成吡喃喹啉的外消旋环化

Indium-Catalyzed Intramolecular Hydroamidation of Alkynes: An Exo-Dig Cyclization for the Synthesis of Pyranoquinolines through Post-Transformational Reaction.

机构信息

Peptide Chemistry Research Center, K. N. Toosi University of Technology , P.O. Box 15875-4416, Tehran, Iran.

Medical Biology Research Center, Kermanshah University of Medical Sciences , Kermanshah, Iran.

出版信息

Org Lett. 2017 Nov 17;19(22):6124-6127. doi: 10.1021/acs.orglett.7b02603. Epub 2017 Oct 31.

DOI:10.1021/acs.orglett.7b02603
PMID:29087201
Abstract

An efficient approach for the synthesis of pyranoquinolines through the indium-catalyzed activation of alkynes is reported. Intramolecular hydroamidation of alkynes can proceed through alkyne activation by indium(III) and then 6-exo-dig cyclization, leading to a fused pyran ring with high selectivity, high atom economy, and good to excellent yields. The cyclization was accomplished through the oxygen, not the nitrogen, of the amide functional group.

摘要

报道了一种通过铟催化炔烃活化来合成吡喃并喹啉的有效方法。炔烃的分子内氨氢化可以通过三价铟活化炔烃,然后进行 6-endo-dig 环化反应来进行,从而以高选择性、高原子经济性和良好至优异的收率得到稠合的吡喃环。环化反应是通过酰胺官能团的氧原子而不是氮原子完成的。

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