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The von Braun Reaction Applied to Azetidines
Author(s) -
Wright Karen,
Drouillat Bruno,
Menguy Laurence,
Marrot Jérôme,
Couty François
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701443
Subject(s) - chemistry , cyanamide , cyanogen bromide , regioselectivity , alkyl , organic chemistry , cleavage (geology) , bromide , ring (chemistry) , medicinal chemistry , reaction conditions , catalysis , biochemistry , geotechnical engineering , fracture (geology) , engineering , peptide sequence , gene
The von Braun reaction (the reaction of cyanogen bromide with tertiary amines) was applied to a series of functionalized N ‐alkyl‐substituted azetidines. This reaction mainly led to the cleavage of the strained four‐membered ring to produce 3‐bromo N ‐alkyl cyanamides in good yields with variable regioselectivity. The resulting cyanamide products were then employed as original building blocks for the synthesis of nitrogen heterocycles.