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一种通过衣康酰亚胺的环化反应合成氢化咪唑并[1,5 - ]哒嗪的新方法及反应途径的HPLC - HRMS监测

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

作者信息

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

机构信息

Faculty of Chemistry, Voronezh State University, Universitetskaya sq., 1, Voronezh 394018, Russian Federation.

Faculty of Physics and Mathematics and Natural Sciences, RUDN University, Miklukho-Maklaya St., 6, Moscow 117198, Russian Federation.

出版信息

Beilstein J Org Chem. 2017 Nov 30;13:2561-2568. doi: 10.3762/bjoc.13.252. eCollection 2017.

DOI:10.3762/bjoc.13.252
PMID:29259665
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5727784/
Abstract

The novel cascade two-stage reaction between itaconimides and 1,2-diamino-4-phenylimidazole proceeds regio- and chemoselectively to form tetrahydroimidazo[1,5-]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.

摘要

衣康酰亚胺与1,2-二氨基-4-苯基咪唑之间的新型串联两步反应区域选择性和化学选择性地进行，生成四氢咪唑并[1,5 -]哒嗪，包括活化的C = C双键进行亲核C加成以及随后中间体与相关氨基的分子内环化。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ed6/5727784/be118bd81a91/Beilstein_J_Org_Chem-13-2561-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ed6/5727784/445ed58213c7/Beilstein_J_Org_Chem-13-2561-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ed6/5727784/39f373c10334/Beilstein_J_Org_Chem-13-2561-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ed6/5727784/b59a99455245/Beilstein_J_Org_Chem-13-2561-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ed6/5727784/07ba59550194/Beilstein_J_Org_Chem-13-2561-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ed6/5727784/85a3dba89fae/Beilstein_J_Org_Chem-13-2561-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ed6/5727784/be118bd81a91/Beilstein_J_Org_Chem-13-2561-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ed6/5727784/445ed58213c7/Beilstein_J_Org_Chem-13-2561-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ed6/5727784/39f373c10334/Beilstein_J_Org_Chem-13-2561-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ed6/5727784/b59a99455245/Beilstein_J_Org_Chem-13-2561-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ed6/5727784/07ba59550194/Beilstein_J_Org_Chem-13-2561-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ed6/5727784/85a3dba89fae/Beilstein_J_Org_Chem-13-2561-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ed6/5727784/be118bd81a91/Beilstein_J_Org_Chem-13-2561-g007.jpg

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