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J Org Chem. 2018 Aug 17;83(16):9522-9529. doi: 10.1021/acs.joc.8b01249. Epub 2018 Jun 27.

Synthesis of Azolo[1,3,5]triazines via Rhodium(III)-Catalyzed Annulation of N-Azolo Imines and Dioxazolones.

Author information

1
Department of Chemistry , Yale University , 225 Prospect Street , New Haven , Connecticut 06520 , United States.

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.

PMID:
29947517
PMCID:
PMC6097942
[Available on 2019-08-17]
DOI:
10.1021/acs.joc.8b01249

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