NH-1,2,3-triazoles from azidomethyl pivalate and carbamates:: Base-labile N-protecting groups
NH-1,2,3-triazoles from azidomethyl pivalate and carbamates:: Base-labile N-protecting groups
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DOI：
10.1055/s-2005-918944
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发表时间：
2005-11-03
期刊：
影响因子：
2
通讯作者：
Sharpless, KB
中科院分区：
文献类型：
--
作者：
Loren, JC;Krasinski, A;Sharpless, KB
以铜(I)为催化剂，通过末端炔烃与三种N-保护的有机叠氮化合物--叠氮甲酸甲酯、叠氮甲基吗啉-4-羧酸酯和叠氮甲酸甲酯N，N-二乙基氨基甲酸甲酯之间的1，3-偶极环加成反应合成了NH-1，2，3-三氮唑。这些有机叠氮化合物很容易从廉价的商业原料中制备出来，只需一两步，即可在0.1摩尔范围内完成。生成的1，2，3-三唑产物中N-取代基与氢氧化钠水溶液的裂解性质从N-甲基丙戊酸甲酯在室温下10分钟，到室温下24小时，在N-甲基吗啉-4-羧酸盐情况下，到85℃下24小时，在N-甲基二乙基氨基甲酸酯的情况下变化。
NH-1,2,3-triazoles have been prepared via the copper(I)-catalyzed 1,3-dipolar cycloaddition between terminal alkynes and three N-protected organic azides, azidomethyl pivalate, azidomethyl morpholine-4-carboxylate, and azidomethyl N,N-diethylcarbamate. These organic azides were easily prepared on 0.1-mol scale in one or two steps from inexpensive commercially available materials. The cleaving properties of N-substituents in the resulting 1,2,3-triazole products with aqueous sodium hydroxide vary from < 10 minutes at room temperature in the case of N-methyl pivalate, to 24 hours at room temperature in the case of N-methyl morpholine-4-carboxylate, to 24 hours at 85 degrees C in the case of N-methyl diethylcarbamate.