ISSN:
1434-193X
Keywords:
Lithium
;
Lithium trimethylsilyldiazomethane
;
Heterocycles
;
Uracil derivatives
;
Pyrazolo[4,3-d]pyrimidindiones
;
Pyrazolo[4,3-d]pyrimidindiones
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The nucleophilic addition of TMSC(Li)N2 at the low reactive C-5 position of the uracil ring of C-6 substituted uracil derivatives is reported. The ratio of C-5 versus C-6 nucleophilic addition of TMSC(Li)N2 dramatically depends on the stereoelectronic properties of the C-6 substituent. In particular, substituents characterized both by sterically bulky and/or electron-withdrawing (EWG) effects appear to direct the nucleophile mainly (methyl, chloromethyl or halogen) or completely (isopropyl) toward the C-5 position. The fine-tuned substituent selectivity found in the nucleophilic addition of TMSC(Li)N2 to C-6 substituted uracils plays a leading role in the synthesis of new trimethylsilyl-1H-[4,3-d]pyrimidin-5,7-dione derivatives, which can in turn be easily modified through known silicon chemistry.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
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