4-Alkynyl indoles, when treated with a benzylidene malonate or a donor-acceptor cyclopropane in the presence of a zinc halide, furnished 3,4-hexannylated or 3,4-heptannulated products, respectively, in fair to excellent yields. The reaction proceeds via a tandem addition/Conia-ene cyclization.

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http://dx.doi.org/10.1021/acs.orglett.2c01810DOI Listing

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