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

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

Published:2017-11-30 Issue: Volume:13 Page:2561-2568
ISSN:1860-5397
Container-title:Beilstein Journal of Organic Chemistry
language:en
Short-container-title:Beilstein J. Org. Chem.

Author:

Vandyshev Dmitry Yu^ORCID,Shikhaliev Khidmet S^ORCID,Potapov Andrey Yu^ORCID,Krysin Michael Yu^ORCID,Zubkov Fedor I^ORCID,Sapronova Lyudmila V^ORCID

Abstract

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.

Publisher

Beilstein Institut

Subject

Organic Chemistry

Link

https://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-13-252.pdf

Reference37 articles.

1. Discovery of 8-Amino-imidazo[1,5-a]pyrazines as Reversible BTK Inhibitors for the Treatment of Rheumatoid Arthritis

2. Structure based design of novel 6,5 heterobicyclic mitogen-activated protein kinase kinase (MEK) inhibitors leading to the discovery of imidazo[1,5-a] pyrazine G-479

3. Discovery of potent, selective and orally bioavailable imidazo[1,5-a]pyrazine derived ACK1 inhibitors

4. Imidazo[1,5-a]pyrazines: Orally efficacious inhibitors of mTORC1 and mTORC2

5. Synthesis and c-Src inhibitory activity of imidazo[1,5-a]pyrazine derivatives as an agent for treatment of acute ischemic stroke

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