TY - JOUR
T1 - Synthesis of 6-substituted 1-alkoxy-5-alkyluracils
AU - Kim, Dae Kee
AU - Kim, Young Woo
AU - Kim, Key H.
PY - 1997
Y1 - 1997
N2 - Synthesis of 6-substituted 1-alkoxy-5-alkyluracils 2a-c have been achieved from readily accessible 2-alkyl-3,3-di(methylthio)acryloyl chlorides 4a,b in high overall yields. Treatment of 4a,b with silver cyanate followed by reaction of the resulting isocyanates 5a,b with an appropriate alkoxyamine afforded N-alkoxy-N'[2-alkyl-3,3-di(methylthio)acryloyl]ureas 6a,b in 85-88% yields. Cyclization of 6a,b in acetic acid containing methanesulfonuic acid followed by oxidation with 3-chloroperoxybenzoic acid gave high yields of 1-alkoxy-5-alkyl-6-(methylsulfonyl)uracils 9a,b. Nucleophilic addition-elimination reaction of 9a,b with sodium azide, phenylthiol, or phenylselenol produced 6-azido-1-butoxythymine (2a, 98%), 5-ethyl-1-(2-phenoxyethoxy)-6-(phenylthio)uracil (2b, 95%), or 5-ethyl-1-(2-phenoxyethoxy)-6-(phenylselenenyl)uracil (2c, 91%).
AB - Synthesis of 6-substituted 1-alkoxy-5-alkyluracils 2a-c have been achieved from readily accessible 2-alkyl-3,3-di(methylthio)acryloyl chlorides 4a,b in high overall yields. Treatment of 4a,b with silver cyanate followed by reaction of the resulting isocyanates 5a,b with an appropriate alkoxyamine afforded N-alkoxy-N'[2-alkyl-3,3-di(methylthio)acryloyl]ureas 6a,b in 85-88% yields. Cyclization of 6a,b in acetic acid containing methanesulfonuic acid followed by oxidation with 3-chloroperoxybenzoic acid gave high yields of 1-alkoxy-5-alkyl-6-(methylsulfonyl)uracils 9a,b. Nucleophilic addition-elimination reaction of 9a,b with sodium azide, phenylthiol, or phenylselenol produced 6-azido-1-butoxythymine (2a, 98%), 5-ethyl-1-(2-phenoxyethoxy)-6-(phenylthio)uracil (2b, 95%), or 5-ethyl-1-(2-phenoxyethoxy)-6-(phenylselenenyl)uracil (2c, 91%).
UR - http://www.scopus.com/inward/record.url?scp=0030993808&partnerID=8YFLogxK
U2 - 10.1002/jhet.5570340148
DO - 10.1002/jhet.5570340148
M3 - Article
AN - SCOPUS:0030993808
SN - 0022-152X
VL - 34
SP - 311
EP - 314
JO - Journal of Heterocyclic Chemistry
JF - Journal of Heterocyclic Chemistry
IS - 1
ER -