One-Pot DBU-Promoted Synthesis of Hydroacridinones and Spirohexahydropyrimidines

Constantinos G. Neochoritis; Nicolaos Eleftheriadis; Arianna Tsiantou; Julia Stephanidou-Stephanatou; Constantinos A. Tsoleridis

doi:10.1055/s-0033-1339922

Synlett, Table of Contents

Synlett 2013; 24(20): 2768-2772
DOI: 10.1055/s-0033-1339922

letter

One-Pot DBU-Promoted Synthesis of Hydroacridinones and Spirohexahydropyrimidines

Constantinos G. Neochoritis

,

Nicolaos Eleftheriadis

,

Arianna Tsiantou

,

Julia Stephanidou-Stephanatou*

,

Constantinos A. Tsoleridis*

Abstract

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Abstract

The potential hydroacridinone synthesis using simple and inexpensive starting materials, namely 1,3-dicarbonyl compounds, anilines, formaldehyde and DBU as a stoichiometric base was explored. As a result, from the reaction of 1,3-cyclohexanedione and dimedone tetrahydroacridinones were the main reaction products along with small yields of their oxidation products, the dihydroacridinones, whereas in the case of 2-acetylcyclohexanone spirohexahydropyrimidines were isolated in very good yields. Plausible mechanistic schemes for the formation of all products are proposed.

Key words

acridinones - aza-annulation - DBU as catalyst - 1,3-diones - spiropyrimidines

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References

References and Notes
1 New address: C. G. Neochoritis, Department of Drug Design, University of Groningen, Groningen, The Netherlands.
2 New address: N. Eleftheriadis, Groningen Research Institute of Pharmacy, University of Groningen, Groningen, The Netherlands.
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General Experimental Procedure for the DBU-Promoted Mannich Reaction: A mixture of 4-methylaniline (1.0 mmol), formaldehyde (9 equiv, 36% aq solution), DBU (1 equiv) and dimedone (1 equiv) in EtOH (20 mL) was refluxed for 10 min to dissolve all the reactants, and then the reaction mixture was stirred for 3 h at r.t. The solvent was distilled off and the resulting residue was subjected to column chromatography on silica gel using petroleum ether–EtOAc (10:1) as eluent, to give the product 3f along with a small amount of 4f. In an analogous manner, using 2-acetylcyclohexanone (2.0 mmol) product 10b was isolated.

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