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Synthesis 2017; 49(16): 3749-3767
DOI: 10.1055/s-0036-1588812
paper
© Georg Thieme Verlag Stuttgart · New York

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

Vladimir P. Zaytsev*
a   Organic Chemistry Department, RUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation
,
Ekaterina L. Revutskaya
a   Organic Chemistry Department, RUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation
,
Tatiana V. Nikanorova
a   Organic Chemistry Department, RUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation
,
Eugeniya V. Nikitina
a   Organic Chemistry Department, RUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation
,
Pavel V. Dorovatovskii
b   National Research Center ‘Kurchatov Institute’, 1 Acad. Kurchatov Sq., Moscow 123182, Russian Federation
,
Victor N. Khrustalev
c   Inorganic Chemistry Department, RUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation
d   Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov St., Moscow, 119991, Russian Federation   Email: vzaitsev@sci.pfu.edu.ru
,
Niyaz Z. Yagafarov
c   Inorganic Chemistry Department, RUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation
,
Fedor I. Zubkov
a   Organic Chemistry Department, RUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation
,
Alexey V. Varlamov
a   Organic Chemistry Department, RUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation
› Author AffiliationsSupported by: This paper was financially supported by the Ministry of Education and Science of the Russian Federation on the program to improve the competitiveness of Peoples’ Friendship University (RUDN University) among the world’s leading research and education centers in the 2016-2020 (the Agreement number 02.a03.21.0008). The authors are grateful to the Russian Foundation for Basic Research (grant Nos. 13-03-00105 and 15-33-50016).�
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Publication History

Received: 25 March 2017

Accepted after revision: 31 March 2017

Publication Date:
05 May 2017 (online)

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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.

Key words

furans - Diels–Alder reaction - multicomponent reaction - isoindolo[2,1-a]quinazoline - isoindolo[1,2-b]quinazoline - IMDAF

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588812.
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