Short approach to pyrrolopyrazino-, pyrrolodiazepino-isoindoles and their benzo analogues via the IMDAF reaction

Aim and Objective: A new approach to synthesis of isoindoles condensed with other heterocycles and revelation of their spatial structure for biochemistry purposes was the main objective of this research. Material and Method: Starting materials for the proposed method, 1-furyl substituted pyrrolo[1,2-a]pyrazines, pyrrolo[1,2-a][1,4]diazepines and their benzoannulated analogues - 4-furyl substituted pyrrolo[1,2-a]quinoxalines and pyrrolo[1,2-a][1,4]benzodiazepines, were synthesized by known procedures. These compounds, all containing a furfurylamine moiety, were introduced into the tandem acylation/ intramolecular furan Diels-Alder (IMDAF) reaction withα,β-unsaturated acid anhydrides (maleic and citraconic anhydrides). In most cases, the key step - the IMDAF reaction - proceeds diastereospecifically with simultaneous formation of five new stereogenic centers and affording the title compounds in mild conditions with satisfactory overall yields. Results: Consequently a broad series of 10,12a-epoxypyrrolo[2',1':3,4]pyrazino[2,1-a]isoindoles, 11,13a-epoxypyrrolo[ 2',1':3,4][1,4]diazepino[2,1-a]isoindoles, tetrahydro-14bH-12,14a-epoxyisoindolo[2,1-a]pyrrolo[2,1-c]quinoxalines, and tetrahydro-9H,15bH-13,15a-epoxyisoindolo[1,2-c]pyrrolo[1,2-a][1,4]benzodiazepines was synthesized and their space structure was elucidated by X-ray analysis. Conclusion: New effective method for synthesis of isoindoles condensed with various heterocycles was proposed. The method is based on the IMDAF reaction and provided a broad diversity of target molecules with controlled stereochemistry. © 2017 Bentham Science Publishers.

Authors
Zubkov F.I. 1 , Orlova D.N. 1 , Zaytsev V.P. 1 , Voronov A.A. 1 , Nikitina E.V. 1 , Khrustalev V.N. 2, 3 , Novikov R.A.4 , Krasavin M.5 , Varlamov A.V. 1
Publisher
Bentham Science Publishers B.V.
Number of issue
5
Language
English
Pages
733-746
Status
Published
Volume
14
Year
2017
Organizations
  • 1 Organic Chemistry Department, Faculty of Science, RUDN University, 6 Miklukho-Maklaya St, Moscow, 117198, Russian Federation
  • 2 Inorganic Chemistry Department, Faculty of Science, RUDN University, 6 Miklukho-Maklaya St, Moscow, 117198, Russian Federation
  • 3 Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov St, Moscow, 119991, Russian Federation
  • 4 V. A. Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, 32 Vavilov St, Moscow, 119991, Russian Federation
  • 5 Department of Chemistry, St. Petersburg State University, Peterhof198504, Russian Federation
Keywords
Cycloaddition; Diels-Alder reaction; Domino reaction; Furans; IMDAF reaction; Pyrrolodiazepine; Pyrrolopyrazine
Date of creation
19.10.2018
Date of change
12.08.2021
Short link
https://repository.rudn.ru/en/records/article/record/5402/
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