A New Route to the Improved Synthesis of 1-(Alkoxymethyl)-5-alkyl- 6-(arylselenenyl)uracils
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%).
Synthesis and anti-HIV-1 activity of a series of 1-(alkoxymethyl)-5-alkyl-6-(arylselenenyl)uracils and -2-thiouracils
A series of 1-(alkoxymethyl)-5-alkyl-6-(phenylselenenyl)uracils and -2-thiouracils modified at the 3- and/or 5-posiuon of the C-6 phenylselenenyl ring with methyl or fluoro substituent has been synthesized and tested for their ability to inhibit HIV-1 rep
Kim, Dae-Kee,Kim, Young-Woo,Gam, Jongsik,Kim, Ganghyeok,Lim, Jinsoo,Lee, Namkyu,Kim, Hun-Taek,Kim, Key H.
p. 1275 - 1283
(2007/10/03)
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