An Intramolecular Diels-Alder Furan (IMDAF) Approach towards the Synthesis of Isoindolo[2,1- a ]quinazolines and Isoindolo[1,2- b ]quinazolines

An efficient approach to bridged pentacyclic nitrogen heterocycles via the tandem acylation/intramolecular Diels-Alder furan (IMDAF) reaction of 2-furylquinazolinones is described. Reactions of α,β-unsaturated acid anhydrides with 2-furyl-2,3-dihydroquinazolin-4-ones give 6b,9-epoxyisoindolo[2,1- a ]quinazolines in average yields. In this case, the exo -IMDAF reactions proceed with excellent diastereoselectivity giving five stereogenic centers and three new rings in one synthetic step. Isomeric 2,4a-epoxyisoindolo[1,2- b ]quinazolines are obtained by one-pot, three-component condensation reactions of allylamine, isatoic anhydride and furaldehydes involving the same IMDAF reaction as the key step. Some useful transformations including halogenation, hydrogenation, Prilezhaev epoxidation, and esterification of the synthesized epoxyisoindoloquinazolines are also demonstrated. © Georg Thieme Verlag Stuttgart - New York.

Authors
Journal
Number of issue
16
Language
English
Pages
3749-3767
Status
Published
Volume
49
Year
2017
Organizations
  • 1 Organic Chemistry Department, RUDN University, 6 Miklukho-Maklaya St., Moscow, 117198, Russian Federation
  • 2 National Research Center 'Kurchatov Institute', 1 Acad. Kurchatov Sq., Moscow, 123182, Russian Federation
  • 3 Inorganic Chemistry Department, RUDN University, 6 Miklukho-Maklaya St., Moscow, 117198, Russian Federation
  • 4 Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov St., Moscow, 119991, Russian Federation
Keywords
Diels-Alder reaction; furans; IMDAF; isoindolo[1,2- b ]quinazoline; isoindolo[2,1- a ]quinazoline; multicomponent reaction
Date of creation
19.10.2018
Date of change
10.08.2021
Short link
https://repository.rudn.ru/en/records/article/record/5387/
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