Regioselective functionalizations of at the positions N-1 and C-5 of pyrimidine bases = 피리미딘염기의 N-1 및 C-5위치의 자리선택적 관능화반응

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An efficient method for the synthesis of 5-iodonium salts of the substituted pyrimidine nucleosides has been found. It has been exploited that the 5-phenyliodonium salt of the pyrimidine nucleosides cross-couples with various functionalized counter parts, i. e., vinylstannanes, alkynylstannanes, and vinylboronic acid in the presence of palladium catalyst. It has been found that alkylcuprate reagents were rapidly coupled with iodonium salt of uracil derivatives. Palladium catalyzed coupling reaction of 5-phenyliodonium triflate uracils with 2,3-dihydrofuran was carried out in DMF at room temperature afforded C-5 glycoside. Phenylsulfenylation or phenylselenenylation at the 5-position of pyrimidines were successfully achieved by the reaction of diphenyl disulfide or diphenyl diselenide with [bis(trifluoroacetoxy)-iodo]benzene in acetonitrile in good yields. A regioselective allylation at N-1 position of pyrimidine derivatives has been successfully performed by palladium catalyzed coupling of silylated pyrimidines with allyltributyltin in tetrahydrofuran at 65℃.
Advisors
Kim, Yong-Hae김용해
Description
한국과학기술원 : 화학과,
Publisher
한국과학기술원
Issue Date
1998
Identifier
144208/325007 / 000955110
Language
eng
Description

학위논문(박사) - 한국과학기술원 : 화학과, 1998.8, [ ix, 114 p. ]

Keywords

Hypervalent iodines; Pyrimidines bases; Regioselectivity; 자리선택성; 하이퍼발랜트요오드; 피리미딘 염기; N-1 and C-5 positions

URI
http://hdl.handle.net/10203/31491
Link
http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=144208&flag=dissertation
Appears in Collection
CH-Theses_Ph.D.(박사논문)
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