BF<sub>3</sub>‑Mediated C2-Amidation of Quinoline <i>N-</i>Oxides\nEmploying Trifluorodiazoethane and Acetonitrile:\nAccess to 2-<i>N-</i>(Trifluoroethyl)amidoquinolines

A Lewis\nacid-mediated C2-<i>N-</i>trifluoroethylamidation\nof quinolines, employing quinoline <i>N-</i>oxides, trifluorodiazoethane,\nand acetonitrile to forge a new class of <i>N-</i>(quinolin<i>-</i>2-yl)-<i>N-</i>(trifluoroethyl)acetamide is presented\nin this Letter. The reaction proceeds through a carbene generation/nitrile\nylide formation/(3 + 2) cycloaddition/rearrangement cascade to furnish\nquinoline-2-<i>N-</i>(trifluoroethyl)acetamide derivatives\nin high yields.

Publication Details

Journal
Figshare
Published
2024-12-20
DOI
https://doi.org/10.1021/acs.orglett.4c04127.s001
Primary Topic
Fluorine in Organic Chemistry
Type
article
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article

BF3‑Mediated C2-Amidation of Quinoline N-Oxides\nEmploying Trifluorodiazoethane and Acetonitrile:\nAccess to 2-N-(Trifluoroethyl)amidoquinolines

Figshare
Fluorine in Organic Chemistry
article

BF3‑Mediated C2-Amidation of Quinoline N-Oxides\nEmploying Trifluorodiazoethane and Acetonitrile:\nAccess to 2-N-(Trifluoroethyl)amidoquinolines

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Abstract

A Lewis\nacid-mediated C2-<i>N-</i>trifluoroethylamidation\nof quinolines, employing quinoline <i>N-</i>oxides, trifluorodiazoethane,\nand acetonitrile to forge a new class of <i>N-</i>(quinolin<i>-</i>2-yl)-<i>N-</i>(trifluoroethyl)acetamide is presented\nin this Letter. The reaction proceeds through a carbene generation/nitrile\nylide formation/(3 + 2) cycloaddition/rearrangement cascade to furnish\nquinoline-2-<i>N-</i>(trifluoroethyl)acetamide derivatives\nin high yields.

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Fluorine in Organic Chemistry
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BF<sub>3</sub>‑Mediated C2-Amidation of Quinoline <i>N-</i>Oxides\nEmploying Trifluorodiazoethane and Acetonitrile:\nAccess to 2-<i>N-</i>(Trifluoroethyl)amidoquinolines · Figshare (2024) | TGRS Research Map | TGRS