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

doi:10.3390/molecules27185799

Molecules (Sep 2022)

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

DOI: https://doi.org/10.3390/molecules27185799
Journal volume & issue: Vol. 27, no. 18
p. 5799

Abstract

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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.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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