Povarov-Type Reaction Using Methyl as New Input: Direct Synthesis of Substituted Quinolines by I2-Mediated Formal [3 + 2 + 1] Cycloaddition

Qinghe Gao; Shan Liu; Xia Wu; Anxin Wu

doi:10.1021/ol502134u

Povarov-Type Reaction Using Methyl as New Input: Direct Synthesis of Substituted Quinolines by I2-Mediated Formal [3 + 2 + 1] Cycloaddition

Organic Letters ◽

10.1021/ol502134u ◽

2014 ◽

Vol 16 (17) ◽

pp. 4582-4585 ◽

Cited By ~ 67

Author(s):

Qinghe Gao ◽

Shan Liu ◽

Xia Wu ◽

Anxin Wu

Keyword(s):

Direct Synthesis ◽

Type Reaction ◽

Substituted Quinolines

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A Direct Synthesis of γ-, δ-, and ε-Lactones Utilizing SmI2-induced Barbier-type Reaction in the Presence of Hexamethylphosphoric Triamide (HMPA)

Chemistry Letters ◽

10.1246/cl.1987.1487 ◽

1987 ◽

Vol 16 (7) ◽

pp. 1487-1490 ◽

Cited By ~ 48

Author(s):

Kenji Otsubo ◽

Kisa Kawamura ◽

Junji Inanaga ◽

Masaru Yamaguchi

Keyword(s):

Direct Synthesis ◽

Hexamethylphosphoric Triamide ◽

Type Reaction

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Direct Synthesis of α-Amino Amides from N-Alkyl Amines by the Copper-Catalyzed Oxidative Ugi-Type Reaction

Synlett ◽

10.1055/s-0031-1290319 ◽

2012 ◽

Vol 23 (03) ◽

pp. 409-412 ◽

Cited By ~ 8

Author(s):

Chunsong Xie ◽

Jinhua Liu ◽

Xin Ye ◽

Rui Huang

Keyword(s):

Direct Synthesis ◽

Type Reaction ◽

Alkyl Amines ◽

Amino Amides

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An atom economical method for the direct synthesis of quinoline derivatives from substituted o-nitrotoluenes

Chemical Communications ◽

10.1039/c4cc09358e ◽

2015 ◽

Vol 51 (14) ◽

pp. 2911-2914 ◽

Cited By ~ 15

Author(s):

Guiyan Liu ◽

Maocong Yi ◽

Lu Liu ◽

Jingjing Wang ◽

Jianhui Wang

Keyword(s):

Direct Synthesis ◽

Quinoline Derivatives ◽

Reaction Conditions ◽

One Pot ◽

Economical Method ◽

Substituted Quinolines ◽

Acrylic Esters

A one-pot procedure for the preparation of substituted quinolines from substituted o-nitrotoluenes with electron-withdrawing groups and olefins (acrylic esters and acrylonitriles) using a cesium catalyst under mild reaction conditions is reported. The process involves a [2+4] cycloaddition mechanism.

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Step-Controlled Povarov-Type Reaction with 1,2-Dihydroquinolines as Precursors of Dienophiles: Direct Synthesis of Spirocyclic Bi-tetrahydroquinolines and Functionalized 1,2-Dihydroquinolines

Organic Letters ◽

10.1021/acs.orglett.6b03330 ◽

2016 ◽

Vol 19 (1) ◽

pp. 58-61 ◽

Cited By ~ 9

Author(s):

Xuwen Ren ◽

Guangxun Li ◽

Jin Huang ◽

Weidong Wang ◽

Yongpo Zhang ◽

...

Keyword(s):

Direct Synthesis ◽

Type Reaction

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ChemInform Abstract: A Direct Synthesis of γ-, δ-, and ε-Lactones Utilizing SmI2-Induced Barbier-Type Reaction in the Presence of Hexamethylphoshoric Triamide (HMPA).

ChemInform ◽

10.1002/chin.198805246 ◽

1988 ◽

Vol 19 (5) ◽

Author(s):

K. OTSUBO ◽

K. KAWAMURA ◽

J. INANAGA ◽

M. YAMAGUCHI

Keyword(s):

Direct Synthesis ◽

Type Reaction

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A Synthetic and Computational Investigation into the Direct Synthesis of ?-Hydroxymethylated Enones from ?-Keto Phosphonates

Australian Journal of Chemistry ◽

10.1071/ch09301 ◽

2009 ◽

Vol 62 (7) ◽

pp. 720 ◽

Cited By ~ 5

Author(s):

Sarah J. Ryan ◽

Christopher D. Thompson ◽

David W. Lupton

Keyword(s):

Reaction Mechanism ◽

Direct Synthesis ◽

Computational Studies ◽

Computational Investigation ◽

Type Reaction

The synthesis of a range of α-hydroxymethylated enones has been achieved using the Villiéras modification of the Horner–Wadsworth–Emmons (HWE) reaction. Scope, limitations, and mechanistic aspects of this reaction were investigated using a combination of synthetic and computational studies. These investigations support a Schlosser–Corey type reaction mechanism that is balanced between two pathways with the outcome influenced by the steric environment of the substrate.

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