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ChemInform Abstract: Ethyl N-(o-Ethynyl)malonanilide as a Useful Building Block for the Preparation of 3,4-Disubstituted-2(1H)-quinolones, 3,4-Disubstituted- and 2,3,4-Trisubstituted Quinolines.

✍ Scribed by A. ARCADI; S. CACCHI; G. FABRIZI; F. MANNA; P. PACE

Publisher: John Wiley and Sons
Year: 2010
Weight: 44 KB
Volume: 29
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199828177

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✦ Synopsis

Ethyl N-(o-Ethynyl)malonanilide as a Useful Building Block for the Preparation of 3,4-Disubstituted-2(1H)-quinolones, 3,4-Disubstituted- and2,3,4-Trisubstituted Quinolines. -The Pd-catalyzed reaction of the o-ethynylmalonanilides with aryl halides affords disubstituted alkynes. Following intramolecular carbocyclization with NaH leads to quinolones, which are useful intermediates for the preparation of 3,4-disubstituted and 2,3,4-trisubstituted quinolines [cf.

substrate (IVa)]. In situ coupling/cyclization [cf. (XIV)] leads to unsatisfactory results. -

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