Facile selective synthesis of 2-methyl-5-amino-1,2,4-oxadiazolium bromides as further targets for nucleophilic additions

The reaction of aminonitrones R 1 C(NH 2 ) = N + (Me)O − (R 1 = Alk, Ar) with isocyanides R 2 NC (R 2 = Alk, Ar; 1.2 equiv.) and Br 2 (1 equiv.) conducted in CHCl 3 (RT, 5 min) gives 2-methyl-5-amino-1,2,4-oxadiazolium bromides in good to excellent yields (65–95%; 16 examples). These species are hig...

Full description

Saved in:
Bibliographic Details
Published in:New journal of chemistry 2018, Vol.42 (12), p.9373-9376
Main Authors: Il’in, Mikhail V., Bolotin, Dmitrii S., Suslonov, Vitalii V., Kukushkin, Vadim Yu
Format: Article
Language:English
Subjects:
Bromides
Hydrazines
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The reaction of aminonitrones R 1 C(NH 2 ) = N + (Me)O − (R 1 = Alk, Ar) with isocyanides R 2 NC (R 2 = Alk, Ar; 1.2 equiv.) and Br 2 (1 equiv.) conducted in CHCl 3 (RT, 5 min) gives 2-methyl-5-amino-1,2,4-oxadiazolium bromides in good to excellent yields (65–95%; 16 examples). These species are highly electrophilically activated and 5-cyclohexylamino-2-methyl-3-phenyl-1,2,4-oxadiazolium bromide, taken as a model compound for the reactivity study, reacts rapidly under mild conditions with hydroxylamine, hydrazine, or benzamidine, to give 5-cyclohexylamino-3-phenyl-1,2,4-oxadiazole (88%), 5-cyclohexylamino-3-phenyl-1,2,4-triazole (95%), and 2-cyclohexylamino-4,6-diphenyl-1,3,5-triazine (64%), respectively. Treatment of the oxadiazolium salt with excess water provides N -benzoyl- N ′-cyclohexylurea (95%).
ISSN:1144-0546
1369-9261
DOI:10.1039/C8NJ01682H