Palladium-catalyzed synthesis of carcinogenic polycyclic aromatic hydrocarbon epoxide-nucleoside adducts: the first amination of a chloro nucleoside.
Pd-catalyzed coupling of the axially constrained, less reactive benzo[a]pyrene bay-region amino benzoates, derived from the tetrahydro and diol epoxides, with C-6 and C-2 halopurine deoxynucleosides offers an efficient approach to the synthesis of the corresponding nucleoside-epoxide adducts. Also reported are the first examples involving the coupling of a 6-chloropurine deoxynucleoside with these amines, a reaction that is difficult by direct halide displacement. Certain mechanistic aspects of this metal-catalyzed C-N bond formation are also discussed. [reaction--see text]
Lakshman
Mahesh K
MK
Department of Chemistry, City College of CUNY, 138th Street at Convent Avenue, New York, NY 10031-9198, USA. lakshman@sci.ccny.cuny.edu
Gunda
Padmaja
P
D000586:Amination; D002273:Carcinogens / Q000737:chemistry*; D002384:Catalysis; D002713:Chlorine / Q000737:chemistry; D018736:DNA Adducts / Q000138:chemical synthesis* / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry*; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D011084:Polycyclic Aromatic Hydrocarbons / Q000737:chemistry*
D002273:Carcinogens; D018736:DNA Adducts; D004852:Epoxy Compounds; D009705:Nucleosides; D011084:Polycyclic Aromatic Hydrocarbons; D002713:Chlorine; D010165:Palladium