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Molecules 2012, 17(5), 5081-5094; https://doi.org/10.3390/molecules17055081

A Convenient One-Pot Preparation of 2-Methyl-3-(phenylthio- methyl)quinolines from Morita-Baylis-Hillman Adducts and Their Oxidation to the Corresponding Sulfones

Department of Chemistry, National Taiwan Normal University, 88, Sec. 4, Tingchow Road, Taipei 116, Taiwan
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Author to whom correspondence should be addressed.
Received: 7 March 2012 / Revised: 19 April 2012 / Accepted: 20 April 2012 / Published: 3 May 2012
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Abstract

A convenient one-pot preparation of 2-methyl-3-(phenylthiomethyl)quinolines from Morita-Baylis-Hillman adducts via conjugate addition of thiols followed by reductive cyclization with Fe/AcOH was developed. The 2-methyl-3-(phenylthiomethyl)quinolines were transformed into 2-methyl-3-(phenylsulfonylmethyl)quinolines via m-CPBA-mediated oxidation.
Keywords: one-pot procedure; Morita-Baylis-Hillman adducts; quinolines; reductive cyclization; Fe/AcOH one-pot procedure; Morita-Baylis-Hillman adducts; quinolines; reductive cyclization; Fe/AcOH
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Ramesh, C.; Lei, P.-M.; Kavala, V.; Kuo, C.-W.; Yao, C.-F. A Convenient One-Pot Preparation of 2-Methyl-3-(phenylthio- methyl)quinolines from Morita-Baylis-Hillman Adducts and Their Oxidation to the Corresponding Sulfones. Molecules 2012, 17, 5081-5094.

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