ANNELATION OF ISOCYTOSINES BY REACTION WITH METHYL N-CYANOMETHANIMIDATE AND SODIUM METHOXIDE - INFLUENCE OF SUBSTITUTION ON THE COURSE OF THE REACTION AND REARRANGEMENTS
ANNELATION OF ISOCYTOSINES BY REACTION WITH METHYL N-CYANOMETHANIMIDATE AND SODIUM METHOXIDE - INFLUENCE OF SUBSTITUTION ON THE COURSE OF THE REACTION AND REARRANGEMENTS
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DOI：
10.1021/jo00214a014
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发表时间：
1985-01-01
影响因子：
3.6
通讯作者：
LEONARD, NJ
中科院分区：
文献类型：
--
作者：
AGASIMUNDIN, YS;OAKES, FT;LEONARD, NJ
Annelation of isocytosine and 6-substituted isocytosines with methyl N-cyanomethanimidate and sodium methoxide in methanol leads to pyrimidotriazines. The structures of the products reveal substituent influence on the direction of cyclization and rearrangement. The exocylic NH2, newly formed in the cyclization process, may undergo further condensation with methyl N-cyanomethanimidate and sodium methoxide in methanol, and this feature of the reaction can be used for selective monomethylation of the exoheterocyclic NH2. A gentle method for the formation of triflate salts of amines involves treatment of the free bases with trimethylsilyl trifluoromethanesulfonate.
