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Solution-phase parallel synthesis of a diverse library of 1,2-dihydroisoquinolines.

ABSTRACT: Synthesis of a 105 membered library of 1,2-dihydroisoquinolines is described. The 1,2-dihydroisoquinoline compounds have been prepared in good yields using a Lewis acid and organocatalyst-cocatalyzed multicomponent reaction of 2-(1-alkynyl)benzaldehydes, amines, and ketones. Various indoles have also been employed as pronucleophiles, furnishing 1-(3-indolyl)-1,2-dihydroisoquinolines. The halogen functionality present in some of the synthesized compounds allows for further diversification by palladium-catalyzed Suzuki?Miyaura and Sonogashira cross-couplings to give more diversified 1,2-dihydroisoquinoline derivatives.

SUBMITTER: Markina NA 

PROVIDER: S-EPMC3118513 | biostudies-literature | 2011 May

REPOSITORIES: biostudies-literature

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Solution-phase parallel synthesis of a diverse library of 1,2-dihydroisoquinolines.

Markina Nataliya A NA   Mancuso Raffaella R   Neuenswander Benjamin B   Lushington Gerald H GH   Larock Richard C RC  

ACS combinatorial science 20110316 3

Synthesis of a 105 membered library of 1,2-dihydroisoquinolines is described. The 1,2-dihydroisoquinoline compounds have been prepared in good yields using a Lewis acid and organocatalyst-cocatalyzed multicomponent reaction of 2-(1-alkynyl)benzaldehydes, amines, and ketones. Various indoles have also been employed as pronucleophiles, furnishing 1-(3-indolyl)-1,2-dihydroisoquinolines. The halogen functionality present in some of the synthesized compounds allows for further diversification by pall  ...[more]

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