2007
DOI: 10.1002/chin.200725137
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Multicomponent Synthesis of Highly Substituted 2‐Pyridones.

Abstract: Pyridine derivatives R 0380 Multicomponent Synthesis of Highly Substituted 2-Pyridones. -An efficient two-step synthesis of highly functionalized 2-pyridones (VI) involves an Ugi four-component condensation of chromones (I) with a diversity of arylamines (II), isonitriles (III) and cyanoacetic acid (IV) as key step. The chromone moiety in compound (V) is cleaved under basic conditions to close the pyridone ring (VI). -(NEO, A. G.; CARRILLO, R. M.; BARRIGA, S.; MOMAN, E.; MARCACCINI, S.; MARCOS*, C.

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“…1 Since the rebirth of this reaction 30 years ago, many two-or three-step strategies towards nitrogen heterocycles have been reported thanks to the huge functional tolerance of the Ugi coupling used in the first step of these sequences. 2 The application of cyanoacetic acid in Ugi reactions was first explored by Marcaccini et al This initial report on the preparation of pyrrolinones 3 was latter extended by the group and others towards the synthesis of quinolines, 4 pyridones, 5 and pyridazinones. 6 In all studies using this substrate, the multicomponent process is followed by a Knoevenagel reaction involving the cyanoacetamide methylene group and a suitably placed carbonyl functionality.…”
mentioning
confidence: 99%
“…1 Since the rebirth of this reaction 30 years ago, many two-or three-step strategies towards nitrogen heterocycles have been reported thanks to the huge functional tolerance of the Ugi coupling used in the first step of these sequences. 2 The application of cyanoacetic acid in Ugi reactions was first explored by Marcaccini et al This initial report on the preparation of pyrrolinones 3 was latter extended by the group and others towards the synthesis of quinolines, 4 pyridones, 5 and pyridazinones. 6 In all studies using this substrate, the multicomponent process is followed by a Knoevenagel reaction involving the cyanoacetamide methylene group and a suitably placed carbonyl functionality.…”
mentioning
confidence: 99%