Chemoselectivity of [4+2] cycloaddition in n-maleyl-and n-allyl-2,6-difurylpiperidin-4-ones

On the basis of a transition state conformation analysis, an attempt was made to explain the high chemoselectivity of intramolecular [4+2] cycloaddition in 3-alkyl-2,6-difuryl-N-maleylpiperidin-4-ones. It was shown that the thermal Diels-Alder reaction in these piperidine derivatives takes place through the "boat" conformation and leads to the formation of hydrogenated 1-alkyl-4-(2-furyl)-2H-8,10a-epoxy-pyrido[2,1-a]isoindol-2-ones. The alternative regioisomers, 3-alkyl-4-(2-furyl)-2H-8,10a-epoxy-pyrido[2,1-a]isoindol-2-ones, are hardly formed at all. At the same time, the intramolecular Diels-Alder reaction in the isostructural 3-alkyl-N-allyl-2,6-difurylpiperidin-4-ones, takes place non-regioselectively from the "chair" conformation. © 2012 Springer Science+Business Media, Inc.

Authors
Zubkov F.I. 1 , Nikitina E.V. 1 , Zaytsev V.P. 1 , Khrustalev V.N.2 , Novikov R.A.3 , Borisov R.S. 4 , Varlamov A.V. 1
Publisher
Латвийский институт органического синтеза Латвийской академии наук / Springer New York Consultants Bureau
Number of issue
5
Language
English
Pages
785-794
Status
Published
Volume
48
Year
2012
Organizations
  • 1 Peoples' Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation
  • 2 A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St., Moscow 119991, Russian Federation
  • 3 V. A. engel'Gardt Institute of Molecular Biology, Russian Academy of Sciences, 32 Vavilova St., Moscow 119991, Russian Federation
  • 4 A. V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, 29 Leninsky Ave., Moscow 119991, Russian Federation
Keywords
"Boat" conformation; 3a,6-epoxyisoindole; Furan; Furfurylamine; Intramolecular Diels-Alder reaction; Piperidin-4-one; Pyrido[2,1-a]isoindole; Stereochemistry
Date of creation
19.10.2018
Date of change
13.08.2021
Short link
https://repository.rudn.ru/en/records/article/record/2415/
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