Synthesen und chemische Reaktionen von α-Cyano-α-isocyanoalkansäureestern

Marco Bergemann; Richard Neidlein

doi:10.1055/s-1996-4442

Synthesis 1996; 1996(8): 975-980
DOI: 10.1055/s-1996-4442

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Synthesen und chemische Reaktionen von α-Cyano-α-isocyanoalkansäureestern

Marco Bergemann, Richard Neidlein^*

^*Pharmazeutisch-Chemisches Institut der Universität Heidelberg, ImNeuenheimer Feld 364, D-69120 Heidelberg, Germany, Fax +49(6221)546430

Abstract

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Synthesis and Chemical Reactions of α -Cyano -α -isocyanoalkanoic Acids.Caretα-Cyano-α-isocyanoalkanoic acid esters 5 were synthesizedin very good yields starting from alkyl α-cyano-α-(formylamido)acetates 3 by alkylation of theappropriate enolates followed by dehydration with trichloromethylchloroformate(diphosgene)/triethylamine at low temperatures. Bromination of these estersgave α-cyano-α-(dibromomethylideneamino)alkanoicacid esters 6 in quantitative yields. Reduction of 6with magnesium led to 5.

isocyano-cyanocarboxylic acid ester - cyano(dibromomethyleneimino)carboxylic acid ester - Ugi reaction

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