Thermally induced formal [3+2] cyclization of ortho-aminoaryl-tethered alkylidenecyclopropanes: facile synthesis of furoquinoline and thienoquinoline derivatives.

Chem Commun (Camb)

Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Meilong Road No. 130, Shanghai, 200237, China and State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.

Published: February 2016

We have developed a facile synthetic method to access furoquinoline and thienoquinoline derivatives via a thermally induced ring-opening and cyclization reaction from ortho-aminoaryl-tethered alkylidenecyclopropanes with the in situ generation of isocyanates or isothiocyanates. These reactions exhibited excellent yields and functional group tolerance under metal-free conditions.

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http://dx.doi.org/10.1039/c5cc09218cDOI Listing

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