Reductive Cyclization of o-Nitrophenyl Propargyl Alcohols:  Facile Synthesis of Substituted Quinolines^†

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Abstract

Reduction of secondary and tertiary o-nitrophenyl propargyl alcohols followed by acid-catalyzed Meyer−Schuster rearrangement gave 2-substituted and 2,4-disubstituted quinolines, respectively. Tertiary propargyl alcohols gave excellent yields of the quinoline derivative, while the yields of quinolines were slightly reduced when secondary propargyl alcohol derivatives were utilized.

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This article has been cited by 6 ACS Journal articles (5 most recent appear below).

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    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Unexpected Domino Reaction via Pd-Catalyzed Sonogashira Coupling of Benzimidoyl Chlorides with 1,6-Enynes and Cyclization To Synthesize Quinoline Derivatives

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    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

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    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Convergent, Regiospecific Synthesis of Quinolines from o-Aminophenylboronates

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    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Versatile Synthesis of Quinoline-3-Carboxylic Esters and Indol-2-Acetic Esters by Palladium-Catalyzed Carbonylation of 1-(2-Aminoaryl)-2-Yn-1-Ols

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    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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