Selenium Dibromide Click Chemistry: The Efficient Synthesis of Novel Selenabicyclo[3.3.1]nonene-2 and -nonane Derivatives

• Published in: International journal of molecular sciences Vol. 24; no. 24; p. 17485
• Main Authors: Musalov, Maxim V, Amosova, Svetlana V, Potapov, Vladimir A
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 14.12.2023
• Subjects: 9-selenabicyclo[3.3.1]nonene-2; alcohols; amination; amines; Biochemistry; Biological activity; Clinical trials; Drugs; Immunization; Influenza; Metabolism; Reagents; Selenium; selenium dibromide; Severe acute respiratory syndrome coronavirus 2; Viruses; amines; alcohols; amination; 9-selenabicyclo[3.3.1]nonene-2; selenium dibromide
• ISSN: 1422-0067; 1661-6596; 1422-0067
• DOI: 10.3390/ijms242417485

Highly efficient and convenient methods for the preparation of 35 novel derivatives of 9-selenabicyclo[3.3.1]nonane and 9-selenabicyclo[3.3.1]nonene-2 in high yields based on the adduct of the transannular addition of SeBr to 1,5-cyclooctadiene were developed. The methods for the amination of the adduct made it possible to obtain both diamino selenabicyclo[3.3.1]nonane derivatives and their dihydrobromide salts in one step in 88-98% yields. The methods meet the criteria of click chemistry. Compounds with high glutathione peroxidase mimetic activity were found among water-soluble dihydrobromide salts. The selective reaction of 2,6-dibromo-9-selenabicyclo[3.3.1]nonane with acetonitrile to form 6-bromo-9-selenabicyclo[3.3.1]nonene-2 was discovered. The latter compound served as a promising starting material to give rise to the new class of selenabicyclo[3.3.1]nonene-2 derivatives, e.g., 6-alkoxy-9-selenabicyclo[3.3.1]nonenes were obtained in 94-99% yields.