Efficient Conversion of Tertiary Propargylamides into Imidazoles via Hydroamination-Cyclization

A method to convert tertiary N -propargylamides into 1,2,4-trisubstituted imidazoles using ammonium chloride and zinc triflate as the catalyst is reported. The method is convenient, practical and employs conventional heating. It is also applicable to N -propargyl lactams and tends to populate the so...

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 50; no. 15; pp. 3048 - 3058
Main Authors Safrygin, Alexander, Krivosheyeva, Elena, Dar'in, Dmitry, Krasavin, Mikhail
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.08.2018
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
cyclodehydration
N-propargylamides
privileged structures
Lewis acid catalysis
imidazoles
lead-oriented synthesis
DISCOVERY
hydroamination
LEAD
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Summary:A method to convert tertiary N -propargylamides into 1,2,4-trisubstituted imidazoles using ammonium chloride and zinc triflate as the catalyst is reported. The method is convenient, practical and employs conventional heating. It is also applicable to N -propargyl lactams and tends to populate the so-called lead-like' chemistry space.
Bibliography:Russian Science Foundation
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0036-1591599