4.5 Article

Synthesis of quinoline-3-carboxylates by a Rh(II)-catalyzed cyclopropanation-ring expansion reaction of indoles with halodiazoacetates

Journal

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 11, Issue -, Pages 1944-1949

Publisher

BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.11.210

Keywords

catalysis; cyclopropanation; indole; quinoline; Rh(II); ring expansion

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In this letter, we report a novel synthesis of ethyl quinoline-3-carboxylates from reactions between a series of indoles and halodiazoacetates. The formation of the quinoline structure is probably the result of a cyclopropanation at the 2- and 3-positions of the indole followed by ring-opening of the cyclopropane and elimination of H-X.

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