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

doi:10.3390/molecules17055081

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

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

Chintakunta Ramesh, Po-Min Lei, Veerababurao Kavala, Chun-Wei Kuo and Ching-Fa Yao*

Department of Chemistry, National Taiwan Normal University, 88, Sec. 4, Tingchow Road, Taipei 116, Taiwan

* Author to whom correspondence should be addressed.

Received: 7 March 2012; in revised form: 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

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Cite This Article

MDPI and ACS Style

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.

AMA Style

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(5):5081-5094.

Chicago/Turabian Style

Ramesh, Chintakunta; Lei, Po-Min; Kavala, Veerababurao; Kuo, Chun-Wei; Yao, Ching-Fa. 2012. "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 17, no. 5: 5081-5094.

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