TY - JOUR
T1 - Inverse Electron Demand Diels-Alder-Type Heterocycle Syntheses with 1,2,3-Triazine 1-Oxides
T2 - Expanded Versatility
AU - Biswas, Soumen
AU - De Angelis, Luca
AU - Rivera, Gildardo
AU - Arman, Hadi
AU - Doyle, Michael P.
N1 - Publisher Copyright:
© 2023 American Chemical Society.
PY - 2023/2/24
Y1 - 2023/2/24
N2 - 1,2,3-Triazine 1-oxides are remarkably effective substrates for inverse electron demand Diels-Alder reactions. Formed from vinyldiazoacetates via reaction with tert-butyl nitrite, these stable heterocyclic compounds undergo clean nucleophilic addition with amidines to form pyrimidines, with β-ketocarbonyl compounds and related nitrile derivatives to form polysubstituted pyridines and with 3/5-aminopyrazoles to form pyrazolo[1,5-a]pyrimidines, in high yield. These practical reactions are rapid at room temperature, are base catalyzed, and offer a diversity of structural modifications.
AB - 1,2,3-Triazine 1-oxides are remarkably effective substrates for inverse electron demand Diels-Alder reactions. Formed from vinyldiazoacetates via reaction with tert-butyl nitrite, these stable heterocyclic compounds undergo clean nucleophilic addition with amidines to form pyrimidines, with β-ketocarbonyl compounds and related nitrile derivatives to form polysubstituted pyridines and with 3/5-aminopyrazoles to form pyrazolo[1,5-a]pyrimidines, in high yield. These practical reactions are rapid at room temperature, are base catalyzed, and offer a diversity of structural modifications.
UR - http://www.scopus.com/inward/record.url?scp=85148772836&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.2c04360
DO - 10.1021/acs.orglett.2c04360
M3 - Artículo
C2 - 36787541
AN - SCOPUS:85148772836
SN - 1523-7060
VL - 25
SP - 1104
EP - 1108
JO - Organic Letters
JF - Organic Letters
IS - 7
ER -