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[4+2] Cycloaddition of α,β-unsaturated acid anhydrides to 2-furylpiperidin-4-ones: The short route to annulated 8,10a-epoxypyrido[2,1-a]isoindoles

✍ Scribed by Fedor I. Zubkov; Inga K. Airiyan; Anastasiya A. Dzyubenko; Nataliya I. Yudina; Vladimir P. Zaytsev; Eugeniya V. Nikitina; Alexey V. Varlamov; Victor N. Khrustalev; Dmitry G. Grudinin

Publisher
Journal of Heterocyclic Chemistry
Year
2010
Tongue
English
Weight
341 KB
Volume
47
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

magnified image A one‐step preparation procedure of 8,10a‐epoxypyrido[2,1‐a]isoindoles and their 7‐carboxylic derivatives is reported. The key synthetic step includes the intramolecular exo‐Diels–Alder reaction (IMDAF) of N‐furfurylacrylamide, produced in situ from 2‐furylpiperidin‐4‐ones and α,β‐unsaturated acid anhydrides. The synthesis of the title compounds can be performed under mild conditions with a high level of regio‐ and stereoselectivity. The same strategy has been successfully used for the synthesis of 9,11a‐epoxyimidazo[4′,5′:3,4]pyrido[2,1‐a]isoindole‐8‐carboxylic acid from maleic anhydride and the spinacine derivatives – 4‐(2‐furyl)‐4,5,6,7‐tetrahydro‐3__H__‐imidazo[4,5‐c]pyridines. J. Heterocyclic Chem., (2010).

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