Synthesis 2012; 44(8): 1163-1170
DOI: 10.1055/s-0031-1290749
special topic
© Georg Thieme Verlag Stuttgart · New York

A New Route to N1-Substituted Uracil Derivatives Using Hypervalent Iodine

Yuichi Yoshimura*
Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai, 981-8558, Japan, Fax: +81(22)2752013   Email: yoshimura@tohoku-pharm.ac.jp
,
Hiroya Kan-no
Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai, 981-8558, Japan, Fax: +81(22)2752013   Email: yoshimura@tohoku-pharm.ac.jp
,
Y. B. Kiran
Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai, 981-8558, Japan, Fax: +81(22)2752013   Email: yoshimura@tohoku-pharm.ac.jp
,
Yoshihiro Natori
Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai, 981-8558, Japan, Fax: +81(22)2752013   Email: yoshimura@tohoku-pharm.ac.jp
,
Yukako Saito
Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai, 981-8558, Japan, Fax: +81(22)2752013   Email: yoshimura@tohoku-pharm.ac.jp
,
Hiroki Takahata*
Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai, 981-8558, Japan, Fax: +81(22)2752013   Email: yoshimura@tohoku-pharm.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 21 February 2012

Accepted: 24 February 2012

Publication Date:
22 March 2012 (online)

Abstract

In continuation of our previous study, oxidative coupling reactions of uracil with allylsilane or enol ethers were examined using diacetoxyiodobenzene. The reaction of persilylated uracil with 3,4-dihydro-2H-pyran in the presence of TMSOTf and PhI(OAc)2 resulted in the formation of a dihydropyranyluracil derivative, although the yield was low. In an extension of the oxidative coupling reaction, a novel glycosylation reaction using glycal derivatives as substrates was also developed. The treatment of persilylated uracil and 3,4-dihydro-2H-pyran with (PhSe)2 and PhI(OAc)2 in the presence of a catalytic amount of TMSOTf gave a 2,3-anti-derivative of 1-(3-phenylselanyltetrahydropyran-2-yl)uracil stereoselectively and in good yield.

 
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