Metal-Free Tandem Beckmann–Electrophilic Aromatic Substitution Cascade Affording Diaryl Imines, Ketones, Amines, and Quinazolines

Samuel Sarsah; Marlon R. Lutz; Kailyn Chichi Bobb; Daniel Becker

doi:10.1016/j.tetlet.2015.07.095

Metal-Free Tandem Beckmann–Electrophilic Aromatic Substitution Cascade Affording Diaryl Imines, Ketones, Amines, and Quinazolines

Samuel Sarsah, Marlon R. Lutz, Kailyn Chichi Bobb, Daniel Becker

Department of Chemistry and Biochemistry

Loyola University Chicago

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

Abstract

A cascade reaction sequence involving a Beckmann rearrangement on benzophenone oxime followed by an electrophilic aromatic substitution (EAS) on the intermediate nitrilium ion affords N -phenyl diaryl imines that may then be hydrolyzed to ketones, or reduced to the corresponding amines. Reaction with benzonitrile afforded 2,4-diphenylquinazoline through a Beckmann–Ritter–EAS cascade.

Original language	American English
Journal	Chemistry: Faculty Publications and Other Works
Volume	56
Issue number	40
DOIs	https://doi.org/10.1016/j.tetlet.2015.07.095
State	Published - Aug 1 2015

Keywords

Cascade Reaction
Tandem Sequence
Beckmann Rearrangement
Electrophilic Aromatic Substitution
Quinazoline

Disciplines

Biochemistry
Chemistry

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Metal-Free Tandem Beckmann Electrophilic Aromatic Substitution CaFinal published version, 258 KBLicense: Unspecified

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title = "Metal-Free Tandem Beckmann–Electrophilic Aromatic Substitution Cascade Affording Diaryl Imines, Ketones, Amines, and Quinazolines",

abstract = " A cascade reaction sequence involving a Beckmann rearrangement on benzophenone oxime followed by an electrophilic aromatic substitution (EAS) on the intermediate nitrilium ion affords N -phenyl diaryl imines that may then be hydrolyzed to ketones, or reduced to the corresponding amines. Reaction with benzonitrile afforded 2,4-diphenylquinazoline through a Beckmann–Ritter–EAS cascade.",

keywords = "Cascade Reaction, Tandem Sequence, Beckmann Rearrangement, Electrophilic Aromatic Substitution, Quinazoline",

author = "Samuel Sarsah and Lutz, {Marlon R.} and Bobb, {Kailyn Chichi} and Daniel Becker",

year = "2015",

month = aug,

day = "1",

doi = "10.1016/j.tetlet.2015.07.095",

language = "American English",

volume = "56",

journal = "Chemistry: Faculty Publications and Other Works",

number = "40",

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TY - JOUR

T1 - Metal-Free Tandem Beckmann–Electrophilic Aromatic Substitution Cascade Affording Diaryl Imines, Ketones, Amines, and Quinazolines

AU - Sarsah, Samuel

AU - Lutz, Marlon R.

AU - Bobb, Kailyn Chichi

AU - Becker, Daniel

PY - 2015/8/1

Y1 - 2015/8/1

N2 - A cascade reaction sequence involving a Beckmann rearrangement on benzophenone oxime followed by an electrophilic aromatic substitution (EAS) on the intermediate nitrilium ion affords N -phenyl diaryl imines that may then be hydrolyzed to ketones, or reduced to the corresponding amines. Reaction with benzonitrile afforded 2,4-diphenylquinazoline through a Beckmann–Ritter–EAS cascade.

AB - A cascade reaction sequence involving a Beckmann rearrangement on benzophenone oxime followed by an electrophilic aromatic substitution (EAS) on the intermediate nitrilium ion affords N -phenyl diaryl imines that may then be hydrolyzed to ketones, or reduced to the corresponding amines. Reaction with benzonitrile afforded 2,4-diphenylquinazoline through a Beckmann–Ritter–EAS cascade.

KW - Cascade Reaction

KW - Tandem Sequence

KW - Beckmann Rearrangement

KW - Electrophilic Aromatic Substitution

KW - Quinazoline

UR - https://ecommons.luc.edu/chemistry_facpubs/86

U2 - 10.1016/j.tetlet.2015.07.095

DO - 10.1016/j.tetlet.2015.07.095

M3 - Article

VL - 56

JO - Chemistry: Faculty Publications and Other Works

JF - Chemistry: Faculty Publications and Other Works

IS - 40

ER -

Metal-Free Tandem Beckmann–Electrophilic Aromatic Substitution Cascade Affording Diaryl Imines, Ketones, Amines, and Quinazolines

Abstract

Keywords

Disciplines

Access to Document

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