Novel enamine derivatives of 5,6-dihydro-2'-deoxyuridine formed in reductive amination of 5-formyl-2'-deoxyuridine.
Reductive amination of 5-formyl-3',5'-di-O-acetyl-2'-deoxyuridine with primary amines and sodium triacetoxyborohydride (NaBH(OAc)(3)) afforded novel enamine derivatives of 5,6-dihydro-2'-deoxyuridine as a result of unexpected 1,4-conjugate reduction of intermediate Schiff bases in addition to the secondary amine derivatives of 2'-deoxyuridine, typical 1,2-reduction products.
Sochacka
Elzbieta
E
Institute of Organic Chemistry, Technical University of Lodz, Lodz, Poland. ejsochac@p.lodz.pl
Smuga
Damian
D
D000586:Amination; D002082:Butylamines / Q000737:chemistry; D003857:Deoxyuridine / Q000031:analogs & derivatives* / Q000737:chemistry; D008744:Methylamines / Q000737:chemistry; D015394:Molecular Structure; D012545:Schiff Bases / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet
C479982:5,6-dihydro-2'-deoxyuridin-6-yl; D002082:Butylamines; D008744:Methylamines; D012545:Schiff Bases; C061519:5-formyl-2'-deoxyuridine; C027451:methylamine; C032462:n-butylamine; D003857:Deoxyuridine