Affiliation:
1. Department of Medicinal Chemistry, College of Pharmacy, Chongqing Medical University, Chongqing 400016, P.R. China
Abstract
Background:
and objective: As a key pharmacophore, the cyano group widely exists in
a variety of biologically active compounds. Besides, nitriles are also valuable intermediates for
many common functional groups. In this current work, a new synthesis strategy was developed to
obtain nitriles from aldehydes.
Methods:
Using commercially available aldehydes as raw materials, and hydroxylamine and hydrochloride
as nitrogen sources, the corresponding nitrile compounds were successfully synthesized
by the one-pot method through the promotion of imidazole hydrochloride. And it was characterized
by 1H NMR, 13C NMR, and mass spectrometry.
Results:
Various reaction conditions were applied in order to find an optimum and convenient procedure
for the formation of nitriles. The highest yields (95%) were achieved using sulfolane as a
solvent, and imidazole hydrochloride as a promoter.
Conclusion:
In conclusion, we developed a new synthetic method for nitrile compounds from aldehydes.
Twenty seven examples of functionalized nitrile compounds have been synthesized in
good to excellent yields. This methodology features that an environmentally benign imidazole hydrochloride
replaces transition metal catalysts and oxidants required in conventional strategies to
convert aldehydes into nitriles with good functional group tolerability. Further exploration of imidazole
hydrochloride is ongoing in our laboratory.
Publisher
Bentham Science Publishers Ltd.
Subject
Organic Chemistry,Biochemistry
Cited by
1 articles.
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