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Synthesis 2003(10): 1553-1558
DOI: 10.1055/s-2003-40525
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Cristina Faggia, María García-Valverdeb, Stefano Marcaccini*c, Roberto Pepinoc, Ma. Cruz Pozoc
a CRIST, Centro Interdipartimentale di Cristallografia, Università di Firenze, via della Lastruccia 3, 50019 Sesto Fiorentino (FI), Italy
b Departamento de Química, Facultad de Ciencias, Universidad de Burgos, Plaza Misael Bañuelos s/n, 09001 Burgos, Spain
c Dipartimento di Chimica Organica ‘Ugo Schiff’, Università di Firenze, via della Lastruccia 13, 50019 Sesto Fiorentino (FI), Italy
e-Mail: stefano.marcaccini@unifi.it;
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Publikationsverlauf

Received 8 March 2003
Publikationsdatum:
08. Juli 2003 (online)

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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.