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

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

doi:10.1021/acs.orglett.1c00205

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

Nantachai Inprung, Michael J James, Richard J K Taylor, William P Unsworth

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English
Pages (from-to)	2063-2068
Journal	Organic letters
Volume	23
Issue number	6
Early online date	1 Mar 2021
DOIs	https://doi.org/10.1021/acs.orglett.1c00205
Publication status	E-pub ahead of print - 1 Mar 2021

Bibliographical note

Access to Document

10.1021/acs.orglett.1c00205Licence: CC BY

Mon cascade paper version 18 revision
© 2021 The Authors. Published by American Chemical Society. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy.
Accepted author manuscript, 900 KBLicence: CC BY-NC

Cite this

@article{b0c1bb7bad6f4e24ad1a69b8de0a29e1,

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

abstract = "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.",

author = "Nantachai Inprung and James, {Michael J} and Taylor, {Richard J K} and Unsworth, {William P}",

note = "{\textcopyright} 2021 The Authors. Published by American Chemical Society. This is an author-produced version of the published paper. Uploaded in accordance with the publisher{\textquoteright}s self-archiving policy. ",

year = "2021",

month = mar,

day = "1",

doi = "10.1021/acs.orglett.1c00205",

language = "English",

volume = "23",

pages = "2063--2068",

journal = "Organic letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "6",

}

TY - JOUR

T1 - A Thiol-Mediated Three-Step Ring Expansion Cascade for the Conversion of Indoles into Functionalized Quinolines

AU - Inprung, Nantachai

AU - James, Michael J

AU - Taylor, Richard J K

AU - Unsworth, William P

PY - 2021/3/1

Y1 - 2021/3/1

N2 - 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.

AB - 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.

U2 - 10.1021/acs.orglett.1c00205

DO - 10.1021/acs.orglett.1c00205

M3 - Article

C2 - 33645997

SN - 1523-7060

VL - 23

SP - 2063

EP - 2068

JO - Organic letters

JF - Organic letters

IS - 6

ER -