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

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 H(2)O(2) into corresponding diselenides. Novel organoselenium derivatives were characterized by the (1)H, (77)Se, and (13)C NMR spectro...

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Autores principales: Osmanov, Vladimir K., Chipinsky, Evgeniy V., Khrustalev, Victor N., Novikov, Alexander S., Askerov, Rizvan Kamiloglu, Chizhov, Alexander O., Borisova, Galina N., Borisov, Alexander V., Grishina, Maria M., Kurasova, Margarita N., Kirichuk, Anatoly A., Peregudov, Alexander S., Kritchenkov, Andreii S., Tskhovrebov, Alexander G.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9504104/
https://www.ncbi.nlm.nih.gov/pubmed/36144534
http://dx.doi.org/10.3390/molecules27185799
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author Osmanov, Vladimir K.
Chipinsky, Evgeniy V.
Khrustalev, Victor N.
Novikov, Alexander S.
Askerov, Rizvan Kamiloglu
Chizhov, Alexander O.
Borisova, Galina N.
Borisov, Alexander V.
Grishina, Maria M.
Kurasova, Margarita N.
Kirichuk, Anatoly A.
Peregudov, Alexander S.
Kritchenkov, Andreii S.
Tskhovrebov, Alexander G.
author_facet Osmanov, Vladimir K.
Chipinsky, Evgeniy V.
Khrustalev, Victor N.
Novikov, Alexander S.
Askerov, Rizvan Kamiloglu
Chizhov, Alexander O.
Borisova, Galina N.
Borisov, Alexander V.
Grishina, Maria M.
Kurasova, Margarita N.
Kirichuk, Anatoly A.
Peregudov, Alexander S.
Kritchenkov, Andreii S.
Tskhovrebov, Alexander G.
author_sort Osmanov, Vladimir K.
collection PubMed
description 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 H(2)O(2) into corresponding diselenides. Novel organoselenium derivatives were characterized by the (1)H, (77)Se, and (13)C 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.
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spelling pubmed-95041042022-09-24 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 Osmanov, Vladimir K. Chipinsky, Evgeniy V. Khrustalev, Victor N. Novikov, Alexander S. Askerov, Rizvan Kamiloglu Chizhov, Alexander O. Borisova, Galina N. Borisov, Alexander V. Grishina, Maria M. Kurasova, Margarita N. Kirichuk, Anatoly A. Peregudov, Alexander S. Kritchenkov, Andreii S. Tskhovrebov, Alexander G. Molecules Article 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 H(2)O(2) into corresponding diselenides. Novel organoselenium derivatives were characterized by the (1)H, (77)Se, and (13)C 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. MDPI 2022-09-07 /pmc/articles/PMC9504104/ /pubmed/36144534 http://dx.doi.org/10.3390/molecules27185799 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Osmanov, Vladimir K.
Chipinsky, Evgeniy V.
Khrustalev, Victor N.
Novikov, Alexander S.
Askerov, Rizvan Kamiloglu
Chizhov, Alexander O.
Borisova, Galina N.
Borisov, Alexander V.
Grishina, Maria M.
Kurasova, Margarita N.
Kirichuk, Anatoly A.
Peregudov, Alexander S.
Kritchenkov, Andreii S.
Tskhovrebov, Alexander G.
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
title 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
title_full 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
title_fullStr 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
title_full_unstemmed 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
title_short 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
title_sort 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
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9504104/
https://www.ncbi.nlm.nih.gov/pubmed/36144534
http://dx.doi.org/10.3390/molecules27185799
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