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

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Vinogradova, Ekaterina E., Gazieva, Galina A., Izmest'ev, Alexei N., Karnoukhova, Valentina A., Kravchenko, Angelina N.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9038022/
https://www.ncbi.nlm.nih.gov/pubmed/35480725
http://dx.doi.org/10.1039/d1ra05568b
_version_ 1784693844006141952
author Vinogradova, Ekaterina E.
Gazieva, Galina A.
Izmest'ev, Alexei N.
Karnoukhova, Valentina A.
Kravchenko, Angelina N.
author_facet Vinogradova, Ekaterina E.
Gazieva, Galina A.
Izmest'ev, Alexei N.
Karnoukhova, Valentina A.
Kravchenko, Angelina N.
author_sort Vinogradova, Ekaterina E.
collection PubMed
description 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.
format Online
Article
Text
id pubmed-9038022
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher The Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-90380222022-04-26 Dimroth-type N/S-interchange of N-aminothioglycolurils in the synthesis of 2-hydrazonoimidazo[4,5-d]thiazolones Vinogradova, Ekaterina E. Gazieva, Galina A. Izmest'ev, Alexei N. Karnoukhova, Valentina A. Kravchenko, Angelina N. RSC Adv Chemistry 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. The Royal Society of Chemistry 2021-08-23 /pmc/articles/PMC9038022/ /pubmed/35480725 http://dx.doi.org/10.1039/d1ra05568b Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Vinogradova, Ekaterina E.
Gazieva, Galina A.
Izmest'ev, Alexei N.
Karnoukhova, Valentina A.
Kravchenko, Angelina N.
Dimroth-type N/S-interchange of N-aminothioglycolurils in the synthesis of 2-hydrazonoimidazo[4,5-d]thiazolones
title Dimroth-type N/S-interchange of N-aminothioglycolurils in the synthesis of 2-hydrazonoimidazo[4,5-d]thiazolones
title_full Dimroth-type N/S-interchange of N-aminothioglycolurils in the synthesis of 2-hydrazonoimidazo[4,5-d]thiazolones
title_fullStr Dimroth-type N/S-interchange of N-aminothioglycolurils in the synthesis of 2-hydrazonoimidazo[4,5-d]thiazolones
title_full_unstemmed Dimroth-type N/S-interchange of N-aminothioglycolurils in the synthesis of 2-hydrazonoimidazo[4,5-d]thiazolones
title_short Dimroth-type N/S-interchange of N-aminothioglycolurils in the synthesis of 2-hydrazonoimidazo[4,5-d]thiazolones
title_sort dimroth-type n/s-interchange of n-aminothioglycolurils in the synthesis of 2-hydrazonoimidazo[4,5-d]thiazolones
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9038022/
https://www.ncbi.nlm.nih.gov/pubmed/35480725
http://dx.doi.org/10.1039/d1ra05568b
work_keys_str_mv AT vinogradovaekaterinae dimrothtypensinterchangeofnaminothioglycolurilsinthesynthesisof2hydrazonoimidazo45dthiazolones
AT gazievagalinaa dimrothtypensinterchangeofnaminothioglycolurilsinthesynthesisof2hydrazonoimidazo45dthiazolones
AT izmestevalexein dimrothtypensinterchangeofnaminothioglycolurilsinthesynthesisof2hydrazonoimidazo45dthiazolones
AT karnoukhovavalentinaa dimrothtypensinterchangeofnaminothioglycolurilsinthesynthesisof2hydrazonoimidazo45dthiazolones
AT kravchenkoangelinan dimrothtypensinterchangeofnaminothioglycolurilsinthesynthesisof2hydrazonoimidazo45dthiazolones

Ejemplares similares