Straightforward Access to the Nitric Oxide Donor Azasydnone Scaffold by Cascade Reactions of Amines

Egor S Zhilin; Dmitry M Bystrov; Ivan V Ananyev; Leonid L Fershtat; Nina N Makhova

doi:10.1002/chem.201903526

Straightforward Access to the Nitric Oxide Donor Azasydnone Scaffold by Cascade Reactions of Amines

Chemistry. 2019 Nov 13;25(63):14284-14289. doi: 10.1002/chem.201903526. Epub 2019 Oct 17.

Authors

Egor S Zhilin¹, Dmitry M Bystrov¹, Ivan V Ananyev², Leonid L Fershtat¹, Nina N Makhova¹

Affiliations

¹ N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991, Moscow, Russia.
² A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilova str. 28, 119991, Moscow, Russia.

PMID: 31508851
DOI: 10.1002/chem.201903526

Abstract

A novel one-pot cascade method for the assembly of valuable NO-donor azasydnone scaffold has been developed. The construction strategy involves a diazotization/azo coupling/elimination/double rearrangement cascade sequence of readily available amines. The current protocol enables the generation of a diverse array of azasydnones, including previously hardly accessible heteroaryl substituted azasydnones (25 examples, 70-97 % yield) with a good functional group tolerance under very mild conditions. Preliminary NO-releasing studies revealed an ability of azasydnones to produce NO in a wide range of concentrations. This method provides a new approach to nitrogen-oxygen heterocycles with potential applications in medicine and material science.

Keywords: NO-donors; azasydnone; cascade reactions; homogeneous catalysis; nitrogen heterocycles.

Abstract

Grants and funding