Base-Promoted Synthesis of Quinoline-4(1H)‑thiones from o‑Alkynylanilines and Aroyl Isothiocyanates

A base-promoted synthesis of quinoline-4­(1H)-thiones has been accomplished from the in situ generated o-alkynylthiourea, obtained by reacting o-alkynylanilines with aroyl/acyl isothiocyanates. A 6-exo-dig S-cyclization of the in situ generated thiourea is followed by a rearrangement to give quinoli...

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Bibliographic Details
Published in:Organic letters 2017-11, Vol.19 (22), p.6128-6131
Main Authors: Modi, Anju, Sau, Prasenjit, Patel, Bhisma K.
Format: Article
Language:English
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Summary:A base-promoted synthesis of quinoline-4­(1H)-thiones has been accomplished from the in situ generated o-alkynylthiourea, obtained by reacting o-alkynylanilines with aroyl/acyl isothiocyanates. A 6-exo-dig S-cyclization of the in situ generated thiourea is followed by a rearrangement to give quinoline-4­(1H)-thiones.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b02993