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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 11, 1981 - Issue 10
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Original Articles

Blocking-Deblocking of the NH-Functionality of Uracil and its Derivatives

Pages 787-794 | Published online: 05 Dec 2006
 

Abstract

We have been interested in various 5,6-dihydrouracils and 5,6-dihydroorotic acid derivatives as possible inhibitors of dihydrouracil dehydrogenase, dihydroorotase, and dihydroorotate dehydrogenase.2 The known methods for the synthesis of 5,6-dihydrouracils and 5,6-dihydroorotic acid derivatives are either a low yield cyclization process3 or a catalytic hydrogenation4 procedure which frequently led to the elimination of desired functionality5. In order to obviate these difficulties, we have recently developed6 a mild non-catalytic method for the reduction of 5,6-double bond of uracil and orotic acid derivatives. By using lithium tri-sec-butyl borohydride7–8 we have been able to reduce N1, N3-dialkyl uracil and orotic acid derivatives to the corresponding 5,6-dihydrouracil and orotic acid derivatives as shown in scheme (1).

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