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ID 34214
フルテキストURL
著者
Islam, Rafiqul Department of Drug Discovery and Development, Division of Pharmaceutical Sciences, Graduate School of Medicine, Dentistry, and Pharmaceutica­l Sciences, Okayama University
Nagamatsu, Tomohisa Department of Drug Discovery and Development, Division of Pharmaceutical Sciences, Graduate School of Medicine, Dentistry, and Pharmaceutica­l Sciences, Okayama University
抄録

Several alkylating agents, for example alkyl halides and dimethyl sulfate, were employed in aprotic Solvents Under a variety of conditions for the alkylation of mono- and disubstituted 1H- or 3H-[1,2,3]triazolo[4,5-d]pyrimidine-5,7(4H,6H)-diones, which were prepared by cyclization of the appropriate 5,6-diaminouracils with nitrous acid. The alkylation on the triazole ring in the presence of anhydrous potassium carbonate took place simultaneously at the 1- and 2-positions, with alkylation at the 2-position taking priority. Similar alkylation on the pyrimidine ring with an equivalent alkylating reagent took place only at the 4-position. The alkylation of 3,6-disubstituted derivatives at room temperature led to 5-O-alkylation accompanied by 4-N-alkylation, but at high temperature only 4-N-alkylation took place. Reaction of 3,4,6-trisubstituted derivatives with excess alkylating agent at high temperature leads to the formation of 1,4,6-trisubstituted derivatives with elimination of the 3-substituent.

キーワード
8-azaxanthines
triazolopyrimidines
regioselectivity
alkylations
heterocycles
備考
Published with permission from the copyright holder.
This is a author's copy,as published in Synthesis-Stuttgart , 2006 Issue.24 pp.4167-4179
Publisher URL: http://dx.doi.org/10.1055/s-2006-950337
Direct access to Thomson Web of Science record
Copyright © 2008 by Georg Thieme Verlag Stuttgart
発行日
2008-07-10
出版物タイトル
Synthesis-Stuttgart
24号
開始ページ
4167
終了ページ
4179
資料タイプ
学術雑誌論文
言語
English
査読
有り
DOI
Web of Sience KeyUT
Submission Path
organic_chemistry/10