Tetrahedron p. 4015 - 4022 (1987)
Update date:2022-07-30
Topics:
Meij, Paul F.C. van der
Chen, Tjoe B.R.A.
Hilhorst, Ellen
Waard, Eduard R. De
Pandit, Upenda K.
2-Tosyl-1,2,3,12b-tetrahydroimidazo<1,5-f>phenanthridine (6) was prepared in five steps from 6-chloromethylphenanthridine (1) in an overall yield of 50percent.The reaction of 6 with 1,3-dimethyl-6-methylaminouracil (8) in CH3CN/TFA (100:1) at 50-80 deg C, gave a mixture of products from which 1,3-dimethyl-6-methylaminothymine (9a) could be isolated.This constitutes a mimic of the overall dTMP synthase reaction in transferring both a methylene unit and a hydride equivalent from the cofactor model 6 to the 5-position of a uracil derivative.The other products which are formed in the reaction of 6 with 8 are derived from the reaction of the exocyclic intermediate C, formed in the carbon transfer step, with nucleophiles present in the reaction mixture.
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Doi:10.1016/0022-328X(87)80254-1
(1987)Doi:10.1016/S0040-4039(00)96724-8
(1987)Doi:10.1016/S0040-4039(00)95591-6
(1987)Doi:10.1016/S0040-4020(01)80826-7
(1994)Doi:10.1021/ja00225a045
(1988)Doi:10.1021/om990613o
(1999)
