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Article Abstract

We present a short and efficient way of synthesizing two synthetically versatile 4-quinolone-3-carboxylate building blocks by cyclopropanation-ring expansion of 3-chloroindoles with α-halodiazoacetates as the key step. This novel transformation was applied towards the synthesis of the antibiotic drug norfloxacin.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6753669PMC
http://dx.doi.org/10.3762/bjoc.15.212DOI Listing

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We present a short and efficient way of synthesizing two synthetically versatile 4-quinolone-3-carboxylate building blocks by cyclopropanation-ring expansion of 3-chloroindoles with α-halodiazoacetates as the key step. This novel transformation was applied towards the synthesis of the antibiotic drug norfloxacin.

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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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Synthesis of the (-)-TAN-2483B ring system via a D-mannose-derived cyclopropane.

Org Biomol Chem

February 2011

School of Chemical and Physical Sciences, Victoria University of Wellington, PO Box 600, Wellington, New Zealand.

The ring system of the fungal metabolite (-)-TAN-2483B has been synthesised, for the first time, from d-mannose, utilising a cyclopropanation/ring expansion sequence.

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