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 Ching-Fa Yao

Molecules

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

Published: May 2012

A new one-pot method was created to synthesize 2-methyl-3-(phenylthiomethyl)quinolines starting from Morita-Baylis-Hillman adducts by using thiols in a conjugate addition, followed by a reduction process with iron and acetic acid.
The resulting 2-methyl-3-(phenylthiomethyl)quinolines can be further converted into a different compound, specifically 2-methyl-3-(phenylsulfonylmethyl)quinolines.
The transformation into the latter compound is achieved using m-CPBA for oxidation.

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.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268867	PMC
http://dx.doi.org/10.3390/molecules17055081	DOI Listing

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