ChemInform Abstract: Unexpected Regiospecific Reduction of the Double Bond by NaBH₄ in 2‐(1‐Methyl/1H‐benzimidazole‐2‐yl)‐3‐aryl‐acrylonitrile.

Abstract

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7,8-Dichloro-1-oxo-β-carbolines as a Versatile Scaffold for the Development of Potent and Selective Kinase Inhibitors with Unusual Binding Modes

“…In order to address the importance of the 9-methyl substituent in the tetracyclic spiro series, 22 was prepared from 21 and cyclohexanone using our general procedure (Scheme 2A). By employment of triethylbenzylammonium chloride (TEBAC) mediated phase-transfer catalysis, 16 22 can be alkylated with dimethyl sulfate and potassium carbonate in acetonitrile, yielding 9-methyl derivative 9 . This protocol allows for the selective alkylation of the indole nitrogen without affecting the lactam nitrogen and constitutes a feasible alternative to our previously reported procedure for selective N-methylation of 1-oxo-β-carbolines.…”