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Facile Access to 2-Selenoxo-1,2,3,4-tetrahydro-4-quinazolinone Scaffolds and Corresponding Diselenides via Cyclization between Methyl Anthranilate and Isoselenocyanates: Synthesis and Structural Features |
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| Authors: | Vladimir K. Osmanov Evgeniy V. Chipinsky Victor N. Khrustalev Alexander S. Novikov Rizvan Kamiloglu Askerov Alexander O. Chizhov Galina N. Borisova Alexander V. Borisov Maria M. Grishina Margarita N. Kurasova Anatoly A. Kirichuk Alexander S. Peregudov Andreii S. Kritchenkov Alexander G. Tskhovrebov |
| Abstract: | A practical method for the synthesis of 2-selenoxo-1,2,3,4-tetrahydro-4-quinazolinone was reported. The latter compounds were found to undergo facile oxidation with H2O2 into corresponding diselenides. Novel organoselenium derivatives were characterized by the 1H, 77Se, and 13C NMR spectroscopies, high-resolution electrospray ionization mass spectrometry, IR, elemental analyses (C, H, N), and X-ray diffraction analysis for several of them. Novel heterocycles exhibited multiple remarkable chalcogen bonding (ChB) interactions in the solid state, which were studied theoretically. |
| Keywords: | quinazolinones selenium heterocycles chalcogen bonding cyclization isoselenocyanates |