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

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

Molecules. 2022 Sep 7;27(18):5799. doi: 10.3390/molecules27185799.

Authors

Vladimir K Osmanov¹, Evgeniy V Chipinsky¹, Victor N Khrustalev^{2

3}, Alexander S Novikov^{2

4}, Rizvan Kamiloglu Askerov⁵, Alexander O Chizhov³, Galina N Borisova¹, Alexander V Borisov¹, Maria M Grishina², Margarita N Kurasova², Anatoly A Kirichuk², Alexander S Peregudov⁶, Andreii S Kritchenkov², Alexander G Tskhovrebov^{2

7}

Affiliations

¹ Department of Chemistry, R.E. Alekseev Nizhny Novgorod State Technical University, Minin St., 24, 603155 Nizhny Novgorod, Russia.
² Research Institute of Chemistry, Peoples' Friendship University of Russia, Miklukho-Maklaya St., 6, 117198 Moscow, Russia.
³ N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prosp., 47, 119334 Moscow, Russia.
⁴ Institute of Chemistry, Saint Petersburg State University, Universitetskaya Nab., 7/9, 199034 Saint Petersburg, Russia.
⁵ Department of Organic Chemistry, Baku State University, Z. Xalilov, 23, Baku 1148, Azerbaijan.
⁶ Institute of Organoelement Compounds of the Russian Academy of Sciences, Vavilov St., 28, 119991 Moscow, Russia.
⁷ N.N. Semenov Federal Research Center for Chemical Physics, Russian Academy of Sciences, Ul. Kosygina, 4, 119991 Moscow, Russia.

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: chalcogen bonding; cyclization; heterocycles; isoselenocyanates; quinazolinones; selenium.

MeSH terms

Chalcogens*
Cyclization
Hydrogen Peroxide*
Organoselenium Compounds
Quinazolinones
ortho-Aminobenzoates

Substances

Chalcogens
Organoselenium Compounds
Quinazolinones
isoselenocyanate
ortho-Aminobenzoates
4-hydroxyquinazoline
methyl anthranilate
Hydrogen Peroxide

Abstract

MeSH terms

Substances

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