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A new route to the improved synthesis of 1-(alkoxymethyl)-5-alkyl-6-(arylselenenyl)uracils

✍ Scribed by Namkyu Lee; Young-Woo Kim; Key H. Kim; Dae-Kee Kim

Publisher
Journal of Heterocyclic Chemistry
Year
1997
Tongue
English
Weight
418 KB
Volume
34
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

A new route to C‐6‐selenenyl analogs of compound 1a from 5‐alkyl‐6‐chlorouracils 6a‐b has been described. A mild and highly efficient synthesis of 1‐(alkoxymethyl)‐5‐alkyl‐6‐(arylselenenyl)uracils 8a‐e has been accomplished from 6a‐b in good yields using a two step procedure. Silylation of 5‐alkyl‐6‐chlorouracils 6a‐b using N,O‐bis(trimethylsilyl)acetamide followed by regioselective alkylation of the silylated intermediate with ethyl or benzyl chloromethyl ether in dichloromethane afforded the desired 1‐(alkoxymethyl)‐5‐alkyl‐6‐chlorouracils 7a‐d in 88–94% yields. Compounds 7a‐d readily underwent addition‐elimination reaction with an appropriate arylselenol in the presence of ethanolic sodium hyroxide to produce the corresponding 1‐(alkoxymethyl)‐5‐alkyl‐6‐(arylselenenyl)uracils 8a‐e in excellent yields (94–99%).

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