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J Org Chem ; 83(16): 9522-9529, 2018 08 17.
Article in English | MEDLINE | ID: mdl-29947517

ABSTRACT

A wide range of azolo[1,3,5]triazines were obtained by Rh(III)-catalyzed annulation of N-azolo imines and dioxazolones. The reaction proceeds by the first catalytic C-H amidation of an imidoyl C-H bond followed by cyclodehydration. Good yields were obtained for N-azolo imines derived from aminoazoles and aromatic and heteroaromatic aldehydes. A range of dioxazolone amidating reagents were employed to introduce aryl, heteroaryl, and alkyl substituents. The reaction was also performed with a benchtop setup at 1 mmol scale using microwave heating.


Subject(s)
Imines/chemistry , Oxazolone/chemistry , Rhodium/chemistry , Triazines/chemistry , Triazines/chemical synthesis , Chemistry Techniques, Synthetic
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