期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2019, 期 1, 页码 112-117出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201801439
关键词
Azetidines; Cyanamides; Guanidines; Microwave chemistry; Nitrogen heterocycles
资金
- University of Versailles St-Quentin-en-Yvelines
- University Paris-Saclay
- CNRS
3-Bromo N-alkyl cyanamides are accessible in one simple synthetic operation from N-alkyl azetidines reacting with cyanogen bromide. These unexplored building blocks combine two extremely useful electrophilic moieties: an alkyl bromide and a cyanamide. We demonstrate herein that they can be transformed into a range of nitrogen-containing molecules, and especially cyclic guanidines, accessible in enantiomerically pure form. Considering the large structural diversity of available azetidines, this contribution complements the use of these strained heterocycles in diversity-oriented synthesis.
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