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Synthesis 2009(24): 4235-4255  
DOI: 10.1055/s-0029-1217033
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Two-Stage Synthesis of 8,10a-Epoxypyrido[2,1-a]isoindoles: Stereochemistry of the [4+2] Cycloaddition of Maleic Anhydride with 2,6-Difurylpiperidin-4-ones

Fedor I. Zubkov*a, Inga K. Airiyana, Konstantin F. Turchinb, Vladimir P. Zaytseva, Atash V. Gurbanovc, Abel M. Maharramovc, Victor N. Khrustalevd, Alexandr S. Peregudovd, Eugeniya V. Nikitinaa, Alexey V. Varlamova
a Organic Chemistry Department, Russian Peoples Friendship University, Miklukho-Maklaya St. 6, Moscow 117198, Russian Federation
Fax: +7(95)9550779; e-Mail: fzubkov@sci.pfu.edu.ru;
b Center of Drugs Chemistry, All-Russian Institute for Chemical and Pharmaceutical Research, Zubovskaya St. 7, Moscow 119815, Russian Federation
c Baku State University, Z. Khalilov St. 23, Baku 1148, Azerbaijan
d Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov St. 28, Moscow 119991, Russian Federation
Further Information

Publication History

Received 23 June 2009
Publication Date:
12 October 2009 (online)

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Abstract

A new straightforward synthesis of 8,10a-epoxypyrido[2,1-a]isoindoles and their 7-carboxylic acids from 2,6-difuryl-substituted piperidin-4-ones and maleic anhydride or acryloyl chloride via the intramolecular Diels-Alder reaction has been demonstrated. It has been shown that a one-stage synthesis of the title compounds can be performed under mild conditions and with high levels of regio- and stereoselectivity from easily accessible 2-furylpiperidines.

Key words

intramolecular Diels-Alder furan reaction - IMDAF - stereoselective synthesis - furans - 2,6-difurylpiperidin-4-ones - pyrido[2,1-a]isoindoles

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Crystallographic data for 9i, 9i′, and 13a have been deposited with the Cambridge Crystallographic Data Centre, CCDC 719969 - CCDC 719971. Copies of this information may be obtained free of charge from the Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(1223)336033; e-mail: deposit@ccdc.cam.ac.uk or www.ccdc.cam.ac.uk].