Synthesis of α-Substituted Vinylsulfonium Salts and Their Application as Annulation Reagents in the Formation of Epoxide- and Cyclopropane-Fused Heterocycles

Johnathan V. Matlock; Sven P. Fritz; Stephen A. Harrison; Diane M. Coe; Eoghan M. McGarrigle; Varinder K. Aggarwal

doi:10.1021/jo501885z

Synthesis of α-Substituted Vinylsulfonium Salts and Their Application as Annulation Reagents in the Formation of Epoxide- and Cyclopropane-Fused Heterocycles

The Journal of Organic Chemistry ◽

10.1021/jo501885z ◽

2014 ◽

Vol 79 (21) ◽

pp. 10226-10239 ◽

Cited By ~ 30

Author(s):

Johnathan V. Matlock ◽

Sven P. Fritz ◽

Stephen A. Harrison ◽

Diane M. Coe ◽

Eoghan M. McGarrigle ◽

...

Keyword(s):

Fused Heterocycles ◽

Vinylsulfonium Salts

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ChemInform Abstract: Diastereoselective Synthesis of CF3-Substituted, Epoxide-Fused Heterocycles with β-(Trifluoromethyl)vinylsulfonium Salts.

ChemInform ◽

10.1002/chin.201319104 ◽

2013 ◽

Vol 44 (19) ◽

pp. no-no

Author(s):

Sven P. Fritz ◽

Thomas H. West ◽

Eoghan M. McGarrigle ◽

Varinder K. Aggarwal

Keyword(s):

Diastereoselective Synthesis ◽

Fused Heterocycles ◽

Vinylsulfonium Salts

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Diastereoselective Synthesis of CF3-Substituted, Epoxide-Fused Heterocycles with β-(Trifluoromethyl)vinylsulfonium Salts

Organic Letters ◽

10.1021/ol303200n ◽

2012 ◽

Vol 14 (24) ◽

pp. 6370-6373 ◽

Cited By ~ 40

Author(s):

Sven P. Fritz ◽

Thomas H. West ◽

Eoghan M. McGarrigle ◽

Varinder K. Aggarwal

Keyword(s):

Diastereoselective Synthesis ◽

Fused Heterocycles ◽

Vinylsulfonium Salts

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ChemInform Abstract: Synthesis of α-Substituted Vinylsulfonium Salts and Their Application as Annulation Reagents in the Formation of Epoxide- and Cyclopropane-Fused Heterocycles.

ChemInform ◽

10.1002/chin.201516172 ◽

2015 ◽

Vol 46 (16) ◽

pp. no-no

Author(s):

Johnathan V. Matlock ◽

Sven P. Fritz ◽

Stephen A. Harrison ◽

Diane M. Coe ◽

Eoghan M. McGarrigle ◽

...

Keyword(s):

Fused Heterocycles ◽

Vinylsulfonium Salts

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Room Temperature Oxidative C−H Functionalization for Selective Construction of Fused Heterocycles by a Low N-Doped Graphitic Carbon/HFIP Catalyst System

SSRN Electronic Journal ◽

10.2139/ssrn.3732385 ◽

2020 ◽

Author(s):

He Zhao ◽

Jialu Sun ◽

Rongqing Guan ◽

Qinghao Song ◽

Huanfeng Jiang ◽

...

Keyword(s):

Room Temperature ◽

Catalyst System ◽

Graphitic Carbon ◽

Fused Heterocycles

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Aminocoumarins: A Privileged Precursor for the Synthesis of Fused Heterocycles

Current Organic Chemistry ◽

10.2174/1385272823666190514073610 ◽

2019 ◽

Vol 23 (9) ◽

pp. 1045-1075 ◽

Cited By ~ 1

Author(s):

Saigal ◽

Sumbulunnisan Shareef ◽

Habibur Rahman ◽

Md. Musawwer Khan

Keyword(s):

Chemical Reactivity ◽

Structural Systems ◽

Natural Occurrence ◽

Amino Group ◽

Active Compounds ◽

The Past ◽

Fused Heterocycles

Aminocoumarins are one of the important core structural systems, present in several biologically and medicinally active compounds. Owing to its natural occurrence, potential pharmacological applications and remarkable versatility as a privileged precursor, several proficient synthetic protocols have been reported in the literature over the past years. The presence of an amino group and enamine carbon enhances its chemical reactivity and thus such functionality is repeatedly used for the construction of various fused and simple heterocycles. This review highlights the preparation of different aminocoumarins and their applications for the construction of a variety of five, six and eight membered fused heterocycles.

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Synthesis of unsaturated 1,4-heteroatom-containing benzo-fused heterocycles using a sequential isomerization–ring-closing metathesis strategy

Tetrahedron ◽

10.1016/j.tet.2009.10.061 ◽

2009 ◽

Vol 65 (51) ◽

pp. 10650-10659 ◽

Cited By ~ 29

Author(s):

Garreth L. Morgans ◽

E. Lindani Ngidi ◽

Lee G. Madeley ◽

Setshaba D. Khanye ◽

Joseph P. Michael ◽

...

Keyword(s):

Ring Closing Metathesis ◽

Fused Heterocycles

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Annulation of β-naphthols and 4-hydroxycoumarins with vinylsulfonium salts: synthesis of dihydrofuran derivatives

Organic & Biomolecular Chemistry ◽

10.1039/c8ob00293b ◽

2018 ◽

Vol 16 (15) ◽

pp. 2634-2638 ◽

Cited By ~ 8

Author(s):

Zi-cong Chen ◽

Lang Tong ◽

Zhi-bo Du ◽

Zhi-feng Mao ◽

Xue-jing Zhang ◽

...

Keyword(s):

Mild Conditions ◽

Vinylsulfonium Salts

Annulation reaction of vinylsulfonium salts with β-naphthols and 4-hydroxycoumarins provided dihydrofuran derivatives in moderate to good yields under mild conditions.

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