The Study of Nucleophlic and Electrohilic Reaсtions of Bis- and 3-Substituted Chroman-2, 4-Dions
A. A. Shkel *
Chemistry Institute, Saratov State University, Saratov 410012, Russian Federation
O. A. Mazhukina
Chemistry Institute, Saratov State University, Saratov 410012, Russian Federation
O. V. Fedotova
Chemistry Institute, Saratov State University, Saratov 410012, Russian Federation
*Author to whom correspondence should be addressed.
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.
Keywords: Phenylmethylene bis-chromane-2,4-dion, 3-substituted chromane-2,4-dion, (thio) pyrano dichromenes, trioxaoxonium benzonaphthotetracene salts