[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

(Chemical Equation Presented) 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-3H-imidazo[4,5-c]pyridines. © 2010 HeteroCorporation.

Authors
Zubkov F.I. 1 , Airiyan I.K. 1 , Dzyubenko A.A. 1 , Yudina N.I. 1 , Zaytsev V.P. 1 , Nikitina E.V. 1 , Varlamov A.V. 1 , Khrustalev V.N.2 , Grudinin D.G. 3
Journal
Journal of Heterocyclic Chemistry
Publisher
HeteroCorporation
Number of issue
2
Language
English
Pages
400-414
Status
Published
Link
External link
DOI
10.1002/jhet.316
Volume
47
Year
2010
Organizations
  • 1 Organic Chemistry Department, Russian Peoples' Friendship University, Moscow 117198, Russian Federation
  • 2 Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow 119991, Russian Federation
  • 3 Valeant Canada Ltd., 1956 Bourdon St., Montréal, QC H4M 1V1, Canada
Keywords
1 ethyl 4 (2 furyl) 1,3,4,7,8,10b hexahydro 6a methyl 2h 8,10a epoxypyrido[2,1 a]isoindole 2,6(6ah)dione; 1 ethyl 4 (2 furyl) 7 methyl 2,6 dioxo 1,3,4,6,6a,7,8,10b octahydro 2h 8,10a epoxypyrido[2,1 a]isoindole 7 carboxylic acid; 1 ethyl 4 (2 furyl) 7 phenyl 1,3,4,7,8,10b hexahydro 2h 8,10a epoxypyrido[2,1 a]isoindole 2,6(6ah)dione; 1,3,7,8 tetramethyl 4 (5 methyl 2 furyl) 2,6 dioxo 1,3,4,6,6a,7,8,10b octahydro 2h 8,10a epoxypyrido[2,1 a]isoindole 7 carboxylic acid; 1,3,8 trimethyl 4 (5 methyl 2 furyl) 7 phenyl 1,3,4,7,8,10b hexahydro 2h 8,10aepoxypyrido[2,1 a]isoindole 2,6(6ah)dione; 2 (2 furyl) 3,5 dimethyl 6 (2 thienyl)piperidin 4 one; 2 (2 furyl) 3,5 dimethyl 6 phenylpiperidin 4 one; 2 furylpiperidin 4 one derivative; 3,5 dimethyl 2 (5 methyl 2 furyl) 6 phenylpiperidin 4 one; 4 (2 furyl) 1,3,4,7,8, 10b hexahydro 1,3 dimethyl 7 phenyl 2h 8,10a epoxypyrido[2,1 a]isoindole 2,6(6ah)dione; 4 (2 furyl) 1,3,4,7,8, 10b hexahydro 1,3,6a trimethyl 2h 8,10a epoxypyrido[2,1 a]isoindole 2,6(6ah)dione; 4 (2 furyl) 1,3,4,7,8,10b hexahydro 1 methyl 7 phenyl 2h 8,10a epoxypyrido[2,1 a]isoindole 2,6(6ah)dione; 4 (2 furyl) 1,3,4,7,8,10b hexahydro 1,6a dimethyl 2h 8,10a epoxypyrido[2,1 a]isoindole 2,6(6ah)dione; 4 (2 furyl) 1,3,7 trimethyl 2,6 dioxo 1,3,4,6,6a,7,8,10b octahydro 2h 8,10a epoxypyrido[2,1 a]isoindole 7 carboxylic acid; 4 (2 furyl) 1,7 dimethyl 1,3,4,7,8,10b hexahydro 2h 8,10a epoxypyrido[2,1 a]isoindole 2,6(6ah)dione; 4 (2 furyl) 1,7 dimethyl 2,6 dioxo 1,3,4,6,6a,7,8,10b octahydro 2h 8,10a epoxypyrido[2,1 a]isoindole 7 carboxylic acid; 4 (5 methyl 2 furyl) 1,3,4,7,8,10b hexahydro 1,3,6a,8 tetramethyl 2h 8,10a epoxypyrido[2,1 a]isoindole 2,6(6ah)dione; 7 carboxylic derivative; 8,10a epoxypyrido[2,1 a]isoindole derivative; acid anhydride; acrylamide derivative; carboxyl group; carboxylic acid derivative; isoindole derivative; maleic anhydride; methyl 4 (2 furyl) 1,7 dimethyl 2,6 dioxo 1,3,4,6,6a,7,8,10b octahydro 2h 8,10a epoxypyrido[2,1 a]isoindole 7 carboxylate; n furfurylacrylamide; piperidone derivative; pyridine derivative; unclassified drug; unindexed drug; article; cycloaddition; Diels Alder reaction; drug synthesis; stereochemistry
Date of creation
19.10.2018
Date of change
13.08.2021
Short link
https://repository.rudn.ru/en/records/article/record/2805/
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