Abstract
6-Cyanouracil derivatives underwent a direct nucleophilic substitution reaction with alkyl Grignard reagents in the presence of zinc(II) chloride as a catalyst to form the corresponding 6-alkyluracils. This methodology is applicable to sugar-protected 6-cyanouridine and 6-cyano-2′-deoxyuridine without the protection at the N3-imide and provides a facile and general access to versatile 6-alkyluracil and 6-alkyluridine derivatives.
| Original language | English |
|---|---|
| Pages (from-to) | 4027-4036 |
| Number of pages | 10 |
| Journal | Journal of Organic Chemistry |
| Volume | 78 |
| Issue number | 8 |
| DOIs | |
| Publication status | Published - 2013 Apr 19 |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
Synthesis of 6-alkyluridines from 6-cyanouridine via zinc(II) chloride-catalyzed nucleophilic substitution with alkyl grignard reagents. / Shih, Yu Chiao; Yang, Ya Ying; Lin, Chun Chi; Chien, Tun-Cheng.
In: Journal of Organic Chemistry, Vol. 78, No. 8, 19.04.2013, p. 4027-4036.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Synthesis of 6-alkyluridines from 6-cyanouridine via zinc(II) chloride-catalyzed nucleophilic substitution with alkyl grignard reagents
AU - Shih, Yu Chiao
AU - Yang, Ya Ying
AU - Lin, Chun Chi
AU - Chien, Tun-Cheng
PY - 2013/4/19
Y1 - 2013/4/19
N2 - 6-Cyanouracil derivatives underwent a direct nucleophilic substitution reaction with alkyl Grignard reagents in the presence of zinc(II) chloride as a catalyst to form the corresponding 6-alkyluracils. This methodology is applicable to sugar-protected 6-cyanouridine and 6-cyano-2′-deoxyuridine without the protection at the N3-imide and provides a facile and general access to versatile 6-alkyluracil and 6-alkyluridine derivatives.
AB - 6-Cyanouracil derivatives underwent a direct nucleophilic substitution reaction with alkyl Grignard reagents in the presence of zinc(II) chloride as a catalyst to form the corresponding 6-alkyluracils. This methodology is applicable to sugar-protected 6-cyanouridine and 6-cyano-2′-deoxyuridine without the protection at the N3-imide and provides a facile and general access to versatile 6-alkyluracil and 6-alkyluridine derivatives.
UR - http://www.scopus.com/inward/record.url?scp=84876586619&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84876586619&partnerID=8YFLogxK
U2 - 10.1021/jo400364p
DO - 10.1021/jo400364p
M3 - Article
C2 - 23535022
AN - SCOPUS:84876586619
VL - 78
SP - 4027
EP - 4036
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 8
ER -