A Thiol-Mediated Three-Step Ring Expansion Cascade for the Conversion of Indoles into Functionalized Quinolines | Zendy

Nantachai Inprung | Zendy; Michael J. James | Zendy; Richard J. K. Taylor | Zendy; William P. Unsworth | Zendy

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A Thiol-Mediated Three-Step Ring Expansion Cascade for the Conversion of Indoles into Functionalized Quinolines

Author(s) -

Nantachai Inprung,

Michael J. James,

Richard J. K. Taylor,

William P. Unsworth

Publication year - 2021

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.1c00205

Subject(s) - chemistry , thio , indole test , combinatorial chemistry , cascade , ring (chemistry) , reagent , thiol , nucleophile , nucleophilic substitution , nucleophilic aromatic substitution , sn2 reaction , stereochemistry , organic chemistry , catalysis , chromatography

An operationally simple, high yielding three-step cascade process is described for the direct conversion of indole-tethered ynones into functionalized quinolines. A single “multitasking” thiol reagent is used to promote a three-step dearomatizing spirocyclization, nucleophilic substitution, and one-atom ring expansion reaction cascade under remarkably mild conditions. In addition, a novel route to thio-oxindoles is described, which was discovered by serendipity.

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