Heterocyclic Compounds
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ChemInform Abstract: Synthesis and Stereochemistry of Reissert Compounds from Benzothiazole.
First published: August 10, 1993
Abstract
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ChemInform Abstract
Benzothiazole (I) reacts with the aryl chlorides (II) and trimethylsilyl cyanide (III) to yield the Reissert compounds (IV). Further alkylation of their carbanions with methyl iodide (V) generates the 2-substituted derivatives (VI). Conformational analysis of (IVa) by NMR (400 MHz) indicates that the Z- to E-amide conformer ratio is 79:21.
