Insertion of benzene rings into the amide bond: one-step synthesis of acridines and acridones from aryl amides

Didier G. Pintori; Michael F. Greaney

doi:10.1021/ol902568x

Insertion of benzene rings into the amide bond: one-step synthesis of acridines and acridones from aryl amides

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Abstract

"Chemical Equation Presented" Insertion of benzene rings into the amide bond using the reactive intermediate benzyne is described. Aromatic amides undergo smooth insertion when treated with O-triflatophenyl silane benzyne precursors, producing versatile aminobenzophenone products in good to excellent yield. The process is entirely metal-free and has been exemplified on the synthesis of biologically active acridones and acridines. © 2010 American Chemical Society.

Original language	English
Pages (from-to)	168-171
Number of pages	3
Journal	Organic Letters
Volume	12
Issue number	1
DOIs	https://doi.org/10.1021/ol902568x
Publication status	Published - 1 Jan 2010

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title = "Insertion of benzene rings into the amide bond: one-step synthesis of acridines and acridones from aryl amides",

abstract = "{"}Chemical Equation Presented{"} Insertion of benzene rings into the amide bond using the reactive intermediate benzyne is described. Aromatic amides undergo smooth insertion when treated with O-triflatophenyl silane benzyne precursors, producing versatile aminobenzophenone products in good to excellent yield. The process is entirely metal-free and has been exemplified on the synthesis of biologically active acridones and acridines. {\textcopyright} 2010 American Chemical Society.",

author = "Pintori, {Didier G.} and Greaney, {Michael F.}",

note = "CAPLUS AN 2009:1501990(Journal)",

year = "2010",

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AU - Pintori, Didier G.

AU - Greaney, Michael F.

N1 - CAPLUS AN 2009:1501990(Journal)

PY - 2010/1/1

Y1 - 2010/1/1

N2 - "Chemical Equation Presented" Insertion of benzene rings into the amide bond using the reactive intermediate benzyne is described. Aromatic amides undergo smooth insertion when treated with O-triflatophenyl silane benzyne precursors, producing versatile aminobenzophenone products in good to excellent yield. The process is entirely metal-free and has been exemplified on the synthesis of biologically active acridones and acridines. © 2010 American Chemical Society.

AB - "Chemical Equation Presented" Insertion of benzene rings into the amide bond using the reactive intermediate benzyne is described. Aromatic amides undergo smooth insertion when treated with O-triflatophenyl silane benzyne precursors, producing versatile aminobenzophenone products in good to excellent yield. The process is entirely metal-free and has been exemplified on the synthesis of biologically active acridones and acridines. © 2010 American Chemical Society.

U2 - 10.1021/ol902568x

DO - 10.1021/ol902568x

M3 - Article

SN - 1523-7052

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SP - 168

EP - 171

JO - Organic Letters

JF - Organic Letters

IS - 1

ER -

Insertion of benzene rings into the amide bond: one-step synthesis of acridines and acridones from aryl amides

Abstract

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