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Umpolung of Reactivity of Lithium Trimethylsilyldiazomethane at the C-5 Position of 6-Substituted Uracil Derivatives

✍ Scribed by Raffaele Saladino; Luigi Stasi; Rosario Nicoletti; Claudia Crestini; Maurizio Botta

Publisher: John Wiley and Sons
Year: 1999
Tongue: English
Weight: 240 KB
Volume: 1999
Category: Article
ISSN: 1434-193X
DOI: 10.1002/(sici)1099-0690(199911)1999:11<2751::aid-ejoc2751>3.0.co;2-i

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✦ Synopsis

The nucleophilic addition of TMSC(Li)N 2 at the low reactive the nucleophile mainly (methyl, chloromethyl or halogen) or completely (isopropyl) toward the C-5 position. The fine-C-5 position of the uracil ring of C-6 substituted uracil derivatives is reported. The ratio of C-5 versus C-6 tuned substituent selectivity found in the nucleophilic addition of TMSC(Li)N 2 to C-6 substituted uracils plays a nucleophilic addition of TMSC(Li)N 2 dramatically depends on the stereoelectronic properties of the C-6 substituent. In leading role in the synthesis of new trimethylsilyl-1H-[4,3d]pyrimidin-5,7-dione derivatives, which can in turn be particular, substituents characterized both by sterically bulky and/or electron-withdrawing (EWG) effects appear to direct easily modified through known silicon chemistry.

of a cysteine thiolate anion at the C-6 position of dUMP, [a] Dipartimento Agrochimico Agrobiologico, portant 6-substituted uracils, 1-[(2-hydroxyethoxy)methyl]-Universita `della Tuscia, 6-phenylthiothymine (HEPT), [12] and 3,4-dihydro-2-alkoxy-

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