Synthesis of Cyanamides via a One-Pot Oxidation-Cyanation of Primary and Secondary Amines

被引：9
|
作者：
Kuhl, Nadine [1 ]
Raval, Saurin [1 ]
Cohen, Ryan D. [1 ]
机构：
[1] Merck & Co Inc, Dept Proc Res & Dev, Rahway, NJ 07065 USA
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 05期
关键词：
CYANOGEN-BROMIDE; N-CYANATION; ELECTROPHILIC CYANATION; TIEMANN REARRANGEMENT; PRACTICAL SYNTHESIS; BACE1; INHIBITOR; VERUBECESTAT; AMINATION;
D O I：
10.1021/acs.orglett.8b04007
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An operationally simple oxidation cyanation method for the synthesis of cyanamides is described. The procedure utilizes inexpensive and commercially available N-chlorosuccinimide and Zn(CN)(2) as reagents to avoid direct handling of toxic cyanogen halides. It is demonstrated to be amenable for the cyanation of a variety of primary and secondary amines and aniline derivatives as well as a complex synthetic intermediate en route to verubecestat (MK-8931). Additionally, kinetic measurements and other control experiments are reported to shed light onto the mechanism of this cyanation reaction.
引用
收藏
页码：1268 / 1272
页数：5
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