The "Victory" Reaction: A Three Component Synthesis of Pyrido[2,3-d]pyrimidines
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Abstract
Pedro Victory (1928-1994) spent most of his scientific career studying the synthetic applications of 2-methoxy-6-oxo-1,4,5,6-tetrahydropyridin-3-carbonitriles 3.1 The presence of a methoxy group in pyridones 3 in the ß- position of an a,ß-unsaturated cyano group, which is also conjugated with the lactam NH, render such compoundexcellent substrates for the ethylenic nucleophilic substitution.
This approach allowed us to describe genera lprocedures for the synthesis of pyrazolo[3,4-b]pyridines, 1,6-naphthyridines and 4-aminopyrido[2,3-d]pyrimidinesby treatment of 3 with amidine systems 5. More recently, we described an acyclic strategy for the synthesis of compounds 6 based on the isolation of the corresponding Michael adduct 4 that allowed us to obtain 4-oxopyrido[2,3-d]pyrimidines 6 (R3 = OH).2
Pedro Victory (1928-1994) spent most of his scientific career studying the synthetic applications of 2-methoxy-6-oxo-1,4,5,6-tetrahydropyridin-3-carbonitriles 3.1 The presence of a methoxy group in pyridones 3 in the ß- position of an a,ß-unsaturated cyano group, which is also conjugated with the lactam NH, render such compoundexcellent substrates for the ethylenic nucleophilic substitution.
This approach allowed us to describe genera lprocedures for the synthesis of pyrazolo[3,4-b]pyridines, 1,6-naphthyridines and 4-aminopyrido[2,3-d]pyrimidinesby treatment of 3 with amidine systems 5. More recently, we described an acyclic strategy for the synthesis of compounds 6 based on the isolation of the corresponding Michael adduct 4 that allowed us to obtain 4-oxopyrido[2,3-d]pyrimidines 6 (R3 = OH).2
Here, we report our preliminary results that pyridopyrimidines 6 can be obtained in a single step as a result of a one-pot three component reaction using controlled microwave-assisted synthesis (Emrys Synthesizer).
