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Synthesis of 4,6-disubstituted bicyclo[3.3.1]nona-3,6-dien-2-ones

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1. Title Title of document Synthesis of 4,6-disubstituted bicyclo[3.3.1]nona-3,6-dien-2-ones
2. Creator Author's name, affiliation, country S. G Mikhalyonok; Belarusian State Technological University
2. Creator Author's name, affiliation, country V. S Bezborodov; Belarusian State Technological University
2. Creator Author's name, affiliation, country N. M Kuz'menok; Belarusian State Technological University
2. Creator Author's name, affiliation, country A. I Savelyev; Belarusian State Technological University
2. Creator Author's name, affiliation, country A. S Arol; Belarusian State Technological University
3. Subject Discipline(s)
3. Subject Keyword(s) Mannich base; cyclohex-2-enone; Michael addition; aldol condensation; bicyclo[3.3.1]nona-3,6-dien-2-one
4. Description Abstract Bicyclo[3.3.1]nonane system is an important structural motif observed in a diverse natural products. Here, we report a concise synthetic route exploiting aldol condensation reactions for construction bicyclo[3.3.1]nonane ring system. Our strategy employes cyclohex-2-enones bearing another carbonyl group in side chain as key structural unit. The reaction showed good results for substrates bearing electron-donating groups in aromatic substituents. Overall, the described synthesis of bicyclo[3.3.1]nona-3,6-dien-2-ones required 2 steps and only 2 building blocks (such as Mannich base and acetoacetic ester) to access desired bicyclic system.
5. Publisher Organizing agency, location The Russian Academy of Sciences
6. Contributor Sponsor(s)
7. Date (DD-MM-YYYY) 15.07.2023
8. Type Status & genre Peer-reviewed Article
8. Type Type Research Article
9. Format File format
10. Identifier Uniform Resource Identifier https://journals.rcsi.science/0514-7492/article/view/141661
10. Identifier Digital Object Identifier (DOI) 10.31857/S0514749223070078
10. Identifier eLIBRARY Document Number (EDN) HTAMSF
11. Source Title; vol., no. (year) Russian Journal of Organic Chemistry; Vol 59, No 7 (2023)
12. Language English=en ru
13. Relation Supp. Files
14. Coverage Geo-spatial location, chronological period, research sample (gender, age, etc.)
15. Rights Copyright and permissions Copyright (c) 2023 Russian Academy of Sciences