An unusual Michael addition of 3,3-dimethoxypropanenitrile to 2-aryl acrylates: a convenient route to 4-unsubstituted 5,6-dihydropyrido[2,3-d]pyrimidines.
An unusual Michael addition between 2-aryl-substituted acrylates and 3,3-dimethoxypropanenitrile which leads, depending on the reaction temperature (60 or -78 degrees C, respectively), to a 4-methoxymethylene-substituted 4-cyanobutyric ester or to a 4-dimethoxymethyl 4-cyanobutyric ester is described. These compounds can be subsequently converted to 4-unsubstituted pyrido[2,3-d]pyrimidines upon treatment with a guanidine system under microwave irradiation.
Berzosa
Xavier
X
Grup d'Enginyeria Molecular, Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta 390, E-08017 Barcelona, Spain.
Bellatriu
Xavier
X
Teixidó
Jordi
J
Borrell
José I
JI
D000179:Acrylates / Q000737:chemistry*; D016203:CDC2 Protein Kinase / Q000819:agonists / Q000737:chemistry*; D004791:Enzyme Inhibitors / Q000737:chemistry* / Q000494:pharmacology; D004952:Esters; D008872:Microwaves; D008956:Models, Chemical; D015394:Molecular Structure; D019636:Neurodegenerative Diseases / Q000188:drug therapy; D009570:Nitriles / Q000737:chemistry*; D011743:Pyrimidines / Q000138:chemical synthesis / Q000737:chemistry*; D013329:Structure-Activity Relationship; D013696:Temperature
C548184:3,3-dimethoxypropanenitrile; C548186:5,6-dihydropyrido(2,3-d)pyrimidine; D000179:Acrylates; D004791:Enzyme Inhibitors; D004952:Esters; D009570:Nitriles; D011743:Pyrimidines; D016203:CDC2 Protein Kinase