An Intramolecular Diels–Alder Furan (IMDAF) Approach towards the Synthesis of Isoindolo[2,1-a]quinazolines and Isoindolo[1,2-b]quinazolines
Vladimir Zaytsev
1
,
Ekaterina Revutskaya
1
,
Tatiana Nikanorova
1
,
Victor Khrustalev
3, 4
,
Niyaz Yagafarov
3
,
Fedor Zubkov
1
,
Alexey Varlamov
1
2
National Research Center ‘Kurchatov Institute’
|
Publication type: Journal Article
Publication date: 2017-05-05
scimago Q2
wos Q2
SJR: 0.559
CiteScore: 4.6
Impact factor: 2.3
ISSN: 00397881, 1437210X
Catalysis
Organic Chemistry
Abstract
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.
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16
Total citations:
16
Citations from 2024:
3
(18.75%)
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Zaytsev V. et al. An Intramolecular Diels–Alder Furan (IMDAF) Approach towards the Synthesis of Isoindolo[2,1-a]quinazolines and Isoindolo[1,2-b]quinazolines // Synthesis. 2017. Vol. 49. No. 16. pp. 3749-3767.
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Zaytsev V., Revutskaya E., Nikanorova T., Nikitina E., Dorovatovskii P., Khrustalev V., Yagafarov N., Zubkov F., Varlamov A. An Intramolecular Diels–Alder Furan (IMDAF) Approach towards the Synthesis of Isoindolo[2,1-a]quinazolines and Isoindolo[1,2-b]quinazolines // Synthesis. 2017. Vol. 49. No. 16. pp. 3749-3767.
Cite this
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TY - JOUR
DO - 10.1055/s-0036-1588812
UR - https://doi.org/10.1055/s-0036-1588812
TI - An Intramolecular Diels–Alder Furan (IMDAF) Approach towards the Synthesis of Isoindolo[2,1-a]quinazolines and Isoindolo[1,2-b]quinazolines
T2 - Synthesis
AU - Zaytsev, Vladimir
AU - Revutskaya, Ekaterina
AU - Nikanorova, Tatiana
AU - Nikitina, Eugeniya
AU - Dorovatovskii, Pavel
AU - Khrustalev, Victor
AU - Yagafarov, Niyaz
AU - Zubkov, Fedor
AU - Varlamov, Alexey
PY - 2017
DA - 2017/05/05
PB - Georg Thieme Verlag KG
SP - 3749-3767
IS - 16
VL - 49
SN - 0039-7881
SN - 1437-210X
ER -
Cite this
BibTex (up to 50 authors)
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@article{2017_Zaytsev,
author = {Vladimir Zaytsev and Ekaterina Revutskaya and Tatiana Nikanorova and Eugeniya Nikitina and Pavel Dorovatovskii and Victor Khrustalev and Niyaz Yagafarov and Fedor Zubkov and Alexey Varlamov},
title = {An Intramolecular Diels–Alder Furan (IMDAF) Approach towards the Synthesis of Isoindolo[2,1-a]quinazolines and Isoindolo[1,2-b]quinazolines},
journal = {Synthesis},
year = {2017},
volume = {49},
publisher = {Georg Thieme Verlag KG},
month = {may},
url = {https://doi.org/10.1055/s-0036-1588812},
number = {16},
pages = {3749--3767},
doi = {10.1055/s-0036-1588812}
}
Cite this
MLA
Copy
Zaytsev, Vladimir, et al. “An Intramolecular Diels–Alder Furan (IMDAF) Approach towards the Synthesis of Isoindolo[2,1-a]quinazolines and Isoindolo[1,2-b]quinazolines.” Synthesis, vol. 49, no. 16, May. 2017, pp. 3749-3767. https://doi.org/10.1055/s-0036-1588812.