Dimroth-type N/S-interchange of N-aminothioglycolurils in the synthesis of 2-hydrazonoimidazo[4,5-d]thiazolones

Dimroth-type N/S-interchange of N-aminothioglycolurils in the synthesis of 2-hydrazonoimidazo[4,5-d]thiazolones Full article

Journal

RSC Advances
ISSN: 2046-2069

Output data

Year: 2021, Volume: 11, Number: 45, Pages: 28395-28400 Pages count : 6 DOI: 10.1039/d1ra05568b

Authors

Vinogradova Ekaterina E. ¹ , Gazieva Galina A. ¹ , Izmest'ev Alexei N. ¹ , Karnoukhova Valentina A. ² , Kravchenko Angelina N. ^1,3

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prosp., 47, Moscow 119991, Russian Federation
2	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilova Str., 28, Moscow 119991, Russian Federation
3	Plekhanov Russian University of Economics, Stremyanny Lane, 36, Moscow 117997, Russian Federation

An original method for the synthesis of 2-hydrazonoimidazo[4,5-d]thiazolone derivatives has been developed based on a one-pot acid-induced sequence of hydrazone formation from 3-thioxoperhydroimidazo[4,5-e]-1,2,4-triazinones and aromatic aldehydes, triazine ring contraction to imidazolidine one, and Dimroth-type N/S-interchange of N-aminothioglycolurils formed in situ into 2-hydrazonoimidazo[4,5-d]thiazolones. 3-Phenylacroleine derivatives are also suitable substrates for the reaction with thioxoperhydroimidazotriazinones.

Vinogradova E.E. , Gazieva G.A. , Izmest'ev A.N. , Karnoukhova V.A. , Kravchenko A.N.
Dimroth-type N/S-interchange of N-aminothioglycolurils in the synthesis of 2-hydrazonoimidazo[4,5-d]thiazolones
RSC Advances. 2021. V.11. N45. P.28395-28400. DOI: 10.1039/d1ra05568b WOS Scopus OpenAlex

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