Reinvestigation of ortho-amidoacetophenones' cyclization mediated by trimethylsilyl trifluoromethanesulfonate. the Lewis-acid-assisted and Brønsted-acid-catalyzed reaction

Yi Ru Chen; Yu Cheng Cho; Tzenge Lien Shih

doi:10.1016/j.tet.2016.02.068

Reinvestigation of ortho-amidoacetophenones' cyclization mediated by trimethylsilyl trifluoromethanesulfonate. the Lewis-acid-assisted and Brønsted-acid-catalyzed reaction

Yi Ru Chen
, Yu Cheng Cho
, Tzenge Lien Shih^*

^*Corresponding author for this work

Tamkang University

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

2 Scopus citations

Abstract

Reinvestigation the synthesis of quinolones from ortho-amidoacetophenones by trimethylsilyl trifluoromethanesulfonate (TMSOTf) mediated reaction is reported. In addition to receiving the expected quinolones, an unexpected intermolecular self-condensation adduct was also isolated. The detailed mechanism of its formation is discussed.

Original language	English
Pages (from-to)	2006-2011
Number of pages	6
Journal	Tetrahedron
Volume	72
Issue number	16
DOIs	https://doi.org/10.1016/j.tet.2016.02.068
State	Published - 21 04 2016
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2016 Elsevier Ltd.

Keywords

Lewis-acid-assisted and Brønsted-acid-catalyzed reaction
Methylquinoline
Quinolone
Trifluoromethanesulfonic acid
Trimethylsilyl trifluoromethanesulfonate

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10.1016/j.tet.2016.02.068

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title = "Reinvestigation of ortho-amidoacetophenones' cyclization mediated by trimethylsilyl trifluoromethanesulfonate. the Lewis-acid-assisted and Br{\o}nsted-acid-catalyzed reaction",

abstract = "Reinvestigation the synthesis of quinolones from ortho-amidoacetophenones by trimethylsilyl trifluoromethanesulfonate (TMSOTf) mediated reaction is reported. In addition to receiving the expected quinolones, an unexpected intermolecular self-condensation adduct was also isolated. The detailed mechanism of its formation is discussed.",

keywords = "Lewis-acid-assisted and Br{\o}nsted-acid-catalyzed reaction, Methylquinoline, Quinolone, Trifluoromethanesulfonic acid, Trimethylsilyl trifluoromethanesulfonate",

author = "Chen, \{Yi Ru\} and Cho, \{Yu Cheng\} and Shih, \{Tzenge Lien\}",

note = "Publisher Copyright: {\textcopyright} 2016 Elsevier Ltd.",

year = "2016",

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day = "21",

doi = "10.1016/j.tet.2016.02.068",

language = "英语",

volume = "72",

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TY - JOUR

T1 - Reinvestigation of ortho-amidoacetophenones' cyclization mediated by trimethylsilyl trifluoromethanesulfonate. the Lewis-acid-assisted and Brønsted-acid-catalyzed reaction

AU - Chen, Yi Ru

AU - Cho, Yu Cheng

AU - Shih, Tzenge Lien

PY - 2016/4/21

Y1 - 2016/4/21

N2 - Reinvestigation the synthesis of quinolones from ortho-amidoacetophenones by trimethylsilyl trifluoromethanesulfonate (TMSOTf) mediated reaction is reported. In addition to receiving the expected quinolones, an unexpected intermolecular self-condensation adduct was also isolated. The detailed mechanism of its formation is discussed.

AB - Reinvestigation the synthesis of quinolones from ortho-amidoacetophenones by trimethylsilyl trifluoromethanesulfonate (TMSOTf) mediated reaction is reported. In addition to receiving the expected quinolones, an unexpected intermolecular self-condensation adduct was also isolated. The detailed mechanism of its formation is discussed.

KW - Lewis-acid-assisted and Brønsted-acid-catalyzed reaction

KW - Methylquinoline

KW - Quinolone

KW - Trifluoromethanesulfonic acid

KW - Trimethylsilyl trifluoromethanesulfonate

UR - https://www.scopus.com/pages/publications/84960919602

U2 - 10.1016/j.tet.2016.02.068

DO - 10.1016/j.tet.2016.02.068

M3 - 文章

AN - SCOPUS:84960919602

SN - 0040-4020

VL - 72

SP - 2006

EP - 2011

JO - Tetrahedron

JF - Tetrahedron

IS - 16

ER -

Reinvestigation of ortho-amidoacetophenones' cyclization mediated by trimethylsilyl trifluoromethanesulfonate. the Lewis-acid-assisted and Brønsted-acid-catalyzed reaction

Abstract

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Keywords

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