Studies on Isocyanides and Related Compounds: A Facile Synthesis of 1,6-Dihydro-6-oxopyrazine-2-carboxylic Acid Derivatives via Ugi Four-Component Condensation

Abstract

The Ugi four-component condensation (U-4CC) between arylglyoxals 7, amines 6, benzoylformic acid (4) and isocyanides 5 afforded the expected products 8 which were cyclized in a 5+1 fashion with ammonium acetate to give 1,N-disubstituted 4-aryl-1,6-dihydro-6-oxo-5-phenylpyrazine-2-carboxamides 9 in good yields. Evidence for the assigned structures 9 was provided by ¹³C NMR spectra and X-ray analysis of 9a.

Key words

Ugi reaction - cyclizations - heterocycles - isocyanides - pyrazine ring synthesis

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Crystallographic data have been deposited at Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK and are available from there under the deposition number CCDC179438.