Efficient [5+1] Synthesis of 4-Quinolones by Domino Amination and Conjugate Addition Reactions of 1-(2-Fluorophenyl)prop-2-yn-1-ones with Amines

Viktor O. Iaroshenko; Satenik Mkrtchyan; Alexander Villinger

doi:10.1055/s-0032-1316826

Synthesis, Table of Contents

Synthesis 2013; 45(2): 205-218
DOI: 10.1055/s-0032-1316826

paper

Efficient [5+1] Synthesis of 4-Quinolones by Domino Amination and Conjugate Addition Reactions of 1-(2-Fluorophenyl)prop-2-yn-1-ones with Amines

Viktor O. Iaroshenko*

^aInstitut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany Fax: +49(381)49864112 Email: viktor.iaroshenko@uni-rostock.de

^bNational Taras Shevchenko University, 62 Volodymyrska st., Kyiv-33, 01033, Ukraine Email: iva108@googlemail.com

,

Satenik Mkrtchyan

^aInstitut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany Fax: +49(381)49864112 Email: viktor.iaroshenko@uni-rostock.de

,

Alexander Villinger

^aInstitut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany Fax: +49(381)49864112 Email: viktor.iaroshenko@uni-rostock.de

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Abstract

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Abstract

A catalyst-free synthetic approach is described for the synthesis of 4-quinolone derivatives through a tandem amination/conjugated Michael addition sequence of 1-(2-fluorophenyl)prop-2-yn-1-one derivatives. The [5+1]-cyclization proceeds efficiently at a high temperature under an inert atmosphere with lithium carbonate as a base, and it provides a practical route to a diverse range of 4-quinolones. The mechanism was studied in details and several of the intermediates were isolated.

Key words

quinones - ketones - domino reactions - aminations - Michael additions - heterocycles

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References

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13 Crystallographic data (excluding structure factors) for compounds 5g, 5q, 6b, 8b, and 11a have been deposited with the accession numbers 868711, 868712, 868715, 868716, and 907162, respectively, and can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk; Web site: www.ccdc.cam.ac.uk/conts/retrieving.html.

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