Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,320 (Yen only)
Period: This Article can be accessed for 7 days.

Note | Regular issue | Vol 48, No. 12, 1998, pp.2601-2610
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8270
Reactivity of Dimethylphenylsilyllithium toward 5- and 6-Substituted 1,3-Dimethyluracil Derivatives

Raffaele Saladino,* Luigi Stasi, Gabriele Volpe, Rosario Nicoletti, and Maurizio Botta*

*Dipartimento Agrochimico, Universita degli studi di Viterbo "La Tuscia", Via San Camillo de Lellis, 01100 Viterbo, Italy

Abstract

Dimethylphenylsilyllithium (PhMe2SiLi) reacts with 5-substituted 1,3-dimethyluracils by selective addition at the electrophilic C-6 position of the uracil ring to give the corresponding 6-dimethylphenylsilyl-5,6-dihydrouracil derivatives. The reaction of PhMe2SiLi with 6-substituted 1,3-dimethyluracils showed a different selectivity, and an unusual addition at the C-5 position was observed. This synthetic procedure appears to be an efficient entry to a new class of highly functionalized 5,6-dihydro-1,3-dimethyluracils characterized by the presence of a silicon substituent selectively introduced at the C-5 and C-6 positions of the uracil ring.