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Synthesis of oxaazaisowurtzitanes by condensation of 4-dimethylaminobenzenesulfonamide with glyoxal Full article

Journal Tetrahedron
ISSN: 0040-4020
Output data Year: 2020, Volume: 76, Number: 27, Article number : 131298, Pages count : 7 DOI: 10.1016/j.tet.2020.131298
Tags Oxaazatetracyclo[5.5.0.0(3,11).0(5,9)]dodecane isowurtzitanes; Condensation; Nitrogen heterocycles; Aldehydes; Sulfonamides
Authors Paromov Artyom E. 1 , Sysolyatin Sergey 1 , Shchurova Irina A. 1 , Rogova Alla 1 , Malykhin Valeriy V. 1 , Gatilov Yuri 2
Affiliations
1 Laboratory for Chemistry of Nitrogen Compounds, Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences (IPCET SB RAS), Biysk, 659322, Altai Krai, Russia
2 Department of Chemistry, Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, 630090, Russia

Abstract: This study was focused on investigating the formation of N-polysulfonylsubstituted aza- and oxaazaisowurtzitanes via condensation of 4-dimethylaminobenzenesulfonamide with glyoxal and discovering new polyheterocyclic caged systems. More specifically, we explored how a donor substituent incorporated into the para position of the phenylsulfonamide molecule would influence the formation of cage products. Four new oxaazaisowurtzitane derivatives bearing one to three aza groups in the cage were consequently synthesized. A side reaction was found to take place, leading to a product having a non-isowurtzitane structure and four 4-dimethylaminobenzenesulfonyl moieties. The side product was analyzed by X-ray diffraction.
Cite: Paromov A.E. , Sysolyatin S. , Shchurova I.A. , Rogova A. , Malykhin V.V. , Gatilov Y.
Synthesis of oxaazaisowurtzitanes by condensation of 4-dimethylaminobenzenesulfonamide with glyoxal
Tetrahedron. 2020. V.76. N27. 131298 :1-7. DOI: 10.1016/j.tet.2020.131298 WOS Scopus РИНЦ
Dates:
Submitted: Apr 30, 2020
Accepted: May 19, 2020
Published online: May 23, 2020
Published print: Jul 1, 2020
Identifiers:
Web of science WOS:000539486500002
Scopus 2-s2.0-85085551785
Elibrary 45511601
OpenAlex W3027919612
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