Studies on Isocyanides and RelatedCompounds: A Facile Synthesis of 1,6-Dihydro-6-oxopyrazine-2-carboxylicAcid Derivatives via Ugi Four-Component Condensation

Faggi, Cristina; Garcı́a-Valverde, Marı́a; Marcaccini, Stefano; Pepino, Roberto; Pozo, M. Cruz

doi:10.1055/s-2003-40525

Synthesis

2003

DOI: 10.1055/s-2003-40525

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Studies on Isocyanides and RelatedCompounds: A Facile Synthesis of 1,6-Dihydro-6-oxopyrazine-2-carboxylicAcid Derivatives via Ugi Four-Component Condensation

Cristina Faggi¹,

Marı́a Garcı́a-Valverde²,

Stefano Marcaccini³

et al.

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 4aryl-1,6-dihydro-6-oxo-5-phenylpyrazine-2-carboxamides 9 in good yields. Evidence for the assigned structures 9 was provided by 13 C NMR spectra and X-ray analysis of 9a.

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Stefano Marcaccini: a pioneer in isocyanide chemistry

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Stefano Marcaccini was one of the pioneers in the use of isocyanide-based multicomponent reactions in organic synthesis. Throughout his career at the University of Florence he explored many different faces of isocyanide chemistry, especially those geared towards the synthesis of biologically relevant heterocycles. His work inspired many researchers who contributed to other important developments in the field of multicomponent reactions and created a school of synthetic chemists that continues today. In this manuscript we intend to review the articles on isocyanide multicomponent reactions published by Dr. Marcaccini and analyse their influence on the following works by other researchers. With this, we hope to highlight the immense contribution of Stefano Marcaccini to the development of isocyanide chemistry and modern organic synthesis as well as the influence of his research on future generations. We believe that this review will not only be a well-deserved tribute to the figure of Stefano Marcaccini, but will also serve as a useful inspiration for chemists working in this field. Graphical abstract

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Stefano Marcaccini: a pioneer in isocyanide chemistry

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The use of the Ugi four-component condensation

2007

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This protocol describes a procedure for the Ugi four-component condensation. It describes the general mechanism as well as the effects of the nature of the components on the Ugi reaction. It also describes the effects of the reaction conditions on the reaction, along with special procedures and workup. The experimental procedure is exemplified by a description of the preparation of N-cyclohexyl 2-[N-(2-chloroacetyl)-N-(4-chlorobenzyl)]amino-2-(4-chlorophenyl)acetamide, a typical Ugi product, that is subsequently used for the synthesis of a 2,5-diketopiperazine, an example of an important type of pharmaceutical compound. The experimental procedure is then extended to the synthesis of a 1,5-disubstituted tetrazole via Ugi four-component condensation. The protocol describes the preparation and characterization of the new 1-cyclohexyl-5-(1-phenylamino-2-methyl)propyltetrazole. The total time for the synthesis and isolation of the two example reactions in parallel is 3 d.

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Studies on Isocyanides and RelatedCompounds: A Facile Synthesis of 1,6-Dihydro-6-oxopyrazine-2-carboxylicAcid Derivatives via Ugi Four-Component Condensation

Cited by 2 publications

References 4 publications

Stefano Marcaccini: a pioneer in isocyanide chemistry

Stefano Marcaccini: a pioneer in isocyanide chemistry

The use of the Ugi four-component condensation

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