Lewis Acid Catalyzed Tandem Polycyclization of Internal Alkynols and Vinyl Azides.

Org Lett

Shanghai Key Laboratory of Functional Materials Chemistry, Key Lab for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Meilong Road 130, Shanghai 200237, China.

Published: November 2015

A novel Lewis acid catalyzed tandem cyclization reaction of internal alkynols and vinyl azides has been achieved to afford a series of products containing a pyran-based indeno[1,2-c]isochromene scaffold in moderate to high yields. This tandem polycyclization protocol provides a straightforward entry to construct the complex polycyclic skeleton through cycloisomerization, formal [4 + 2] cycloaddition, and an elimination process.

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http://dx.doi.org/10.1021/acs.orglett.5b02556DOI Listing

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