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
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
Affiliations
Vladimir K. Osmanov
Department of Chemistry, R.E. Alekseev Nizhny Novgorod State Technical University, Minin St., 24, 603155 Nizhny Novgorod, Russia
Evgeniy V. Chipinsky
Department of Chemistry, R.E. Alekseev Nizhny Novgorod State Technical University, Minin St., 24, 603155 Nizhny Novgorod, Russia
Victor N. Khrustalev
Research Institute of Chemistry, Peoples’ Friendship University of Russia, Miklukho-Maklaya St., 6, 117198 Moscow, Russia
Alexander S. Novikov
Research Institute of Chemistry, Peoples’ Friendship University of Russia, Miklukho-Maklaya St., 6, 117198 Moscow, Russia
Rizvan Kamiloglu Askerov
Department of Organic Chemistry, Baku State University, Z. Xalilov, 23, Baku 1148, Azerbaijan
Alexander O. Chizhov
N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prosp., 47, 119334 Moscow, Russia
Galina N. Borisova
Department of Chemistry, R.E. Alekseev Nizhny Novgorod State Technical University, Minin St., 24, 603155 Nizhny Novgorod, Russia
Alexander V. Borisov
Department of Chemistry, R.E. Alekseev Nizhny Novgorod State Technical University, Minin St., 24, 603155 Nizhny Novgorod, Russia
Maria M. Grishina
Research Institute of Chemistry, Peoples’ Friendship University of Russia, Miklukho-Maklaya St., 6, 117198 Moscow, Russia
Margarita N. Kurasova
Research Institute of Chemistry, Peoples’ Friendship University of Russia, Miklukho-Maklaya St., 6, 117198 Moscow, Russia
Anatoly A. Kirichuk
Research Institute of Chemistry, Peoples’ Friendship University of Russia, Miklukho-Maklaya St., 6, 117198 Moscow, Russia
Alexander S. Peregudov
Institute of Organoelement Compounds of the Russian Academy of Sciences, Vavilov St., 28, 119991 Moscow, Russia
Andreii S. Kritchenkov
Research Institute of Chemistry, Peoples’ Friendship University of Russia, Miklukho-Maklaya St., 6, 117198 Moscow, Russia
Alexander G. Tskhovrebov
Research Institute of Chemistry, Peoples’ Friendship University of Russia, Miklukho-Maklaya St., 6, 117198 Moscow, Russia
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.
