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Research Article Open access CC BY 3.0

The Study of Nucleophlic and Electrohilic Reaсtions of Bis- and 3-Substituted Chroman-2, 4-Dions

A. A. Shkel, O. A. Mazhukina, O. V. Fedotova

Chemical Science International Journal · pp. 356–363 · Published 4 Jul 2013

10.9734/ACSJ/2013/4645

Abstract

Aims: Here we study nucleophilic and electrophilic reactions of bis- and condensed 3-substituted chroman-2,4-dions to produce polychromeno (thio)pyrans and trioxaoxonium benzonaphthotetracene salts. Place and Duration of Study: Saratov State University, Chemistry Institute, between September 2011 and July 2012. Results: Reactions of phenylmethylene bis-chroman-2,4-dion, 3-substituted chroman-2, 4-dion with nucleophilic and electrophilic reagents were studied. Intramolecular O-heterocyclization to polyheteronuclear systems with key chromeno (thio) pyrano fragments of various saturation degrees is shown to be characteristic of the compounds studied. It is noted that phenylmethylene bis chroman-2,4-dion, under the action of phosphorus pentasulfide and hydrogen sulfide in situ, forms bis chromeno thiopyrans. Conclusion: Optimal heterocyclization conditions for 3-substituted chroman-2,4-dion with boron trifluoride etherate to trioxaoxonium benzonaphthotetracene salts were found.  

Phenylmethylene bis-chromane-2,4-dion 3-substituted chromane-2,4-dion (thio) pyrano dichromenes trioxaoxonium benzonaphthotetracene salts

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Cited by 4

3-(1,3-dioxobutan-1-yl)-2H-chromen-2-one in reactions with electrophilic and nucleophilic reagents

A. A. Shkel’, O. A. Mazhukina, O. V. Fedotova · Russian Journal of General Chemistry · 2014

Chemistry of 1,5-diketones: IV. New aspects of the chemistry of 1,5-Dioxo compounds of the 2H-pyran-2-one series

O. V. Fedotova, A. A. Shkel’, O. A. Mazhukina · Russian Journal of Organic Chemistry · 2015

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