A novel synthetic approach to hydroimidazo[1,5-b]pyridazines by the recyclization of itaconimides and HPLC–HRMS monitoring of the reaction pathway

The novel cascade two-stage reaction between itaconimides and 1,2-diamino-4-phenylimidazole proceeds regio- and chemoselectively to form tetrahydroimidazo[1,5-b]pyridazines and includes nucleophilic C-addition by the activated C=C double bond and subsequent intramolecular recyclization of the interm...

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Autores principales: Vandyshev, Dmitry Yu, Shikhaliev, Khidmet S, Potapov, Andrey Yu, Krysin, Michael Yu, Zubkov, Fedor I, Sapronova, Lyudmila V
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2017
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5727784/
https://www.ncbi.nlm.nih.gov/pubmed/29259665
http://dx.doi.org/10.3762/bjoc.13.252
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author Vandyshev, Dmitry Yu
Shikhaliev, Khidmet S
Potapov, Andrey Yu
Krysin, Michael Yu
Zubkov, Fedor I
Sapronova, Lyudmila V
author_facet Vandyshev, Dmitry Yu
Shikhaliev, Khidmet S
Potapov, Andrey Yu
Krysin, Michael Yu
Zubkov, Fedor I
Sapronova, Lyudmila V
author_sort Vandyshev, Dmitry Yu
collection PubMed
description The novel cascade two-stage reaction between itaconimides and 1,2-diamino-4-phenylimidazole proceeds regio- and chemoselectively to form tetrahydroimidazo[1,5-b]pyridazines and includes nucleophilic C-addition by the activated C=C double bond and subsequent intramolecular recyclization of the intermediate with the amino group involved.
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spelling pubmed-57277842017-12-19 A novel synthetic approach to hydroimidazo[1,5-b]pyridazines by the recyclization of itaconimides and HPLC–HRMS monitoring of the reaction pathway Vandyshev, Dmitry Yu Shikhaliev, Khidmet S Potapov, Andrey Yu Krysin, Michael Yu Zubkov, Fedor I Sapronova, Lyudmila V Beilstein J Org Chem Full Research Paper The novel cascade two-stage reaction between itaconimides and 1,2-diamino-4-phenylimidazole proceeds regio- and chemoselectively to form tetrahydroimidazo[1,5-b]pyridazines and includes nucleophilic C-addition by the activated C=C double bond and subsequent intramolecular recyclization of the intermediate with the amino group involved. Beilstein-Institut 2017-11-30 /pmc/articles/PMC5727784/ /pubmed/29259665 http://dx.doi.org/10.3762/bjoc.13.252 Text en Copyright © 2017, Vandyshev et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Vandyshev, Dmitry Yu
Shikhaliev, Khidmet S
Potapov, Andrey Yu
Krysin, Michael Yu
Zubkov, Fedor I
Sapronova, Lyudmila V
A novel synthetic approach to hydroimidazo[1,5-b]pyridazines by the recyclization of itaconimides and HPLC–HRMS monitoring of the reaction pathway
title A novel synthetic approach to hydroimidazo[1,5-b]pyridazines by the recyclization of itaconimides and HPLC–HRMS monitoring of the reaction pathway
title_full A novel synthetic approach to hydroimidazo[1,5-b]pyridazines by the recyclization of itaconimides and HPLC–HRMS monitoring of the reaction pathway
title_fullStr A novel synthetic approach to hydroimidazo[1,5-b]pyridazines by the recyclization of itaconimides and HPLC–HRMS monitoring of the reaction pathway
title_full_unstemmed A novel synthetic approach to hydroimidazo[1,5-b]pyridazines by the recyclization of itaconimides and HPLC–HRMS monitoring of the reaction pathway
title_short A novel synthetic approach to hydroimidazo[1,5-b]pyridazines by the recyclization of itaconimides and HPLC–HRMS monitoring of the reaction pathway
title_sort novel synthetic approach to hydroimidazo[1,5-b]pyridazines by the recyclization of itaconimides and hplc–hrms monitoring of the reaction pathway
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5727784/
https://www.ncbi.nlm.nih.gov/pubmed/29259665
http://dx.doi.org/10.3762/bjoc.13.252
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