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Synthesis 2002(14): 1969-1972
DOI: 10.1055/s-2002-34374
DOI: 10.1055/s-2002-34374
PAPER
© Georg Thieme Verlag Stuttgart · New York
Metal-mediated Variants of the Passerini Reaction: A New Synthesis of 4-Cyanooxazoles
Further Information
Received
23 April 2002
Publication Date:
26 September 2002 (online)
Publication History
Publication Date:
26 September 2002 (online)
Abstract
When the combination of zinc triflate and chlorotrimethylsilane is substituted for a Brønsted acid, the classic Passerini reaction of carbonyl compounds with t-butyl isonitrile affords an efficient 1:2 condensation product leading to β-hydroxy-α-cyanoenamines 17a-f, which can be transformed into 5-substituted-4-cyanooxazoles 8a-f in one step. In contrast to the corresponding Ti-mediated condensations of carbonyl compounds with t-butyl isonitrile, no cyanohydrins are formed.
Key words
oxazole - Passerini - condensation - isonitrile - combinatorial chemistry
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