One-pot tandem 1,4-1,2-addition of phosphites to quinolines.
Trialkyl and silylated dialkyl phosphites were evaluated as phosphorus nucleophiles for the addition to quinolines in a strong acidic medium allowing consecutive 1,4- and 1,2-addition breaking up the aromatic stabilisation, thereby leading to 2,4-diphosphono-1,2,3,4-tetrahydroquinolines in one single reaction step in moderate to good yields (2-84%).
De Blieck
Ann
A
Research Group SynBioC, Department of Organic Chemistry, Faculty of BioScience Engineering, Coupure Links 653, B-9000 Ghent, Belgium.
Masschelein
Kurt G R
KG
Dhaene
Fréderic
F
Rozycka-Sokolowska
Ewa
E
Marciniak
Bernard
B
Drabowicz
Jozef
J
Stevens
Christian V
CV
D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D010575:Pesticides / Q000138:chemical synthesis* / Q000737:chemistry; D017905:Phosphites / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry
D010575:Pesticides; D017905:Phosphites; D011804:Quinolines