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

Sven P. Fritz; Thomas H. West; Eoghan M. McGarrigle; Varinder K. Aggarwal

doi:10.1021/ol303200n

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: 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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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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Diastereoselective Synthesis of Coumarin‐Based Fused Heterocycles via Intramolecular Diels‐Alder and 1,3‐Dipolar Cycloaddition Reactions

ChemistrySelect ◽

10.1002/slct.202002747 ◽

2020 ◽

Vol 5 (31) ◽

pp. 9834-9838

Author(s):

Abdolali Alizadeh ◽

Behnaz Farajpour ◽

Kaveh Amir Ashjaee Asalemi ◽

Sajad Taghipour

Keyword(s):

Diels Alder ◽

Dipolar Cycloaddition ◽

Cycloaddition Reactions ◽

Diastereoselective Synthesis ◽

Fused Heterocycles

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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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Diastereoselective synthesis of β-amino alcohols with two or three chiral centers.

Tetrahedron Letters ◽

10.1016/s0040-4039(01)94542-3 ◽

1979 ◽

Vol 19 (15) ◽

pp. 1355-1356

Author(s):

R Haro-Ramos

Keyword(s):

Amino Alcohols ◽

Diastereoselective Synthesis ◽

Chiral Centers

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1604096: CeO2 nanoparticles: a robust and reusable heterogeneous catalyst for the diastereoselective synthesis of β-acetamido esters – ESI

Journal of Chemical Research ◽

10.3184/174751916x14683300159522 ◽

2016 ◽

Keyword(s):

Heterogeneous Catalyst ◽

Ceo2 Nanoparticles ◽

Diastereoselective Synthesis

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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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Naturally Occurring Organic Acid-catalyzed Facile Diastereoselective Synthesis of Biologically Active (E)-3-(arylimino)indolin-2-one Derivatives in Water at Room Temperature

Current Organic Chemistry ◽

10.2174/1385272822666190924182538 ◽

2019 ◽

Vol 23 (16) ◽

pp. 1778-1788 ◽

Cited By ~ 5

Author(s):

Gurpreet Kaur ◽

Arvind Singh ◽

Kiran Bala ◽

Mamta Devi ◽

Anjana Kumari ◽

...

Keyword(s):

Room Temperature ◽

Biologically Active ◽

Environmentally Benign ◽

Diastereoselective Synthesis ◽

Substituted Anilines ◽

Reaction Conditions ◽

Naturally Occurring ◽

Acid Catalyzed ◽

Reaction Media ◽

Column Chromatographic

A simple, straightforward and efficient method has been developed for the synthesis of (E)-3-(arylimino)indolin-2-one derivatives and (E)-2-((4-methoxyphenyl)imino)- acenaphthylen-1(2H)-one. The synthesis of these biologically-significant scaffolds was achieved from the reactions of various substituted anilines and isatins or acenaphthaquinone, respectively, using commercially available, environmentally benign and naturally occurring organic acids such as mandelic acid or itaconic acid as catalyst in aqueous medium at room temperature. Mild reaction conditions, energy efficiency, good to excellent yields, environmentally benign conditions, easy isolation of products, no need of column chromatographic separation and the reusability of reaction media are some of the significant features of the present protocol.

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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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