Methyl 12-Methyl-3,9-dinitro-5,6,7,12-tetrahydro-13-oxodibenzo[<i>b</i>.<i>g</i>]bicyclo[3.3.1]nonane-6-carboxylate and Related Compounds
A synthesis of the title compound and related structures is reported. The procedure involves double alkylation of a β-ketoester followed by double S<sub>N</sub>Ar ring closure from the γ carbon to give a dibenzo[3.3.1]bicyclic unit. This paper appears to be the first to generate a mid-si...
| Main Authors: | , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-12-01
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| Series: | Molbank |
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| Online Access: | https://www.mdpi.com/1422-8599/2022/4/M1526 |
| _version_ | 1827637583883010048 |
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| author | Dylan R. Nanney Richard A. Bunce |
| author_facet | Dylan R. Nanney Richard A. Bunce |
| author_sort | Dylan R. Nanney |
| collection | DOAJ |
| description | A synthesis of the title compound and related structures is reported. The procedure involves double alkylation of a β-ketoester followed by double S<sub>N</sub>Ar ring closure from the γ carbon to give a dibenzo[3.3.1]bicyclic unit. This paper appears to be the first to generate a mid-sized bicyclic target by a double S<sub>N</sub>Ar process. The synthesis can be performed in one step, but yields are superior (52–62%) when a two-stage procedure is used. |
| first_indexed | 2024-03-09T16:02:58Z |
| format | Article |
| id | doaj.art-242995059ff94f6b8400196f9c46d29c |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-03-09T16:02:58Z |
| publishDate | 2022-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj.art-242995059ff94f6b8400196f9c46d29c2023-11-24T16:54:47ZengMDPI AGMolbank1422-85992022-12-0120224M152610.3390/M1526Methyl 12-Methyl-3,9-dinitro-5,6,7,12-tetrahydro-13-oxodibenzo[<i>b</i>.<i>g</i>]bicyclo[3.3.1]nonane-6-carboxylate and Related CompoundsDylan R. Nanney0Richard A. Bunce1Department of Chemistry, Oklahoma State University, Stillwater, OK 74078-3071, USADepartment of Chemistry, Oklahoma State University, Stillwater, OK 74078-3071, USAA synthesis of the title compound and related structures is reported. The procedure involves double alkylation of a β-ketoester followed by double S<sub>N</sub>Ar ring closure from the γ carbon to give a dibenzo[3.3.1]bicyclic unit. This paper appears to be the first to generate a mid-sized bicyclic target by a double S<sub>N</sub>Ar process. The synthesis can be performed in one step, but yields are superior (52–62%) when a two-stage procedure is used.https://www.mdpi.com/1422-8599/2022/4/M1526double alkylationdouble S<sub>N</sub>Ar ring closuredibenzo[3.3.1]bicyclic systems |
| spellingShingle | Dylan R. Nanney Richard A. Bunce Methyl 12-Methyl-3,9-dinitro-5,6,7,12-tetrahydro-13-oxodibenzo[<i>b</i>.<i>g</i>]bicyclo[3.3.1]nonane-6-carboxylate and Related Compounds Molbank double alkylation double S<sub>N</sub>Ar ring closure dibenzo[3.3.1]bicyclic systems |
| title | Methyl 12-Methyl-3,9-dinitro-5,6,7,12-tetrahydro-13-oxodibenzo[<i>b</i>.<i>g</i>]bicyclo[3.3.1]nonane-6-carboxylate and Related Compounds |
| title_full | Methyl 12-Methyl-3,9-dinitro-5,6,7,12-tetrahydro-13-oxodibenzo[<i>b</i>.<i>g</i>]bicyclo[3.3.1]nonane-6-carboxylate and Related Compounds |
| title_fullStr | Methyl 12-Methyl-3,9-dinitro-5,6,7,12-tetrahydro-13-oxodibenzo[<i>b</i>.<i>g</i>]bicyclo[3.3.1]nonane-6-carboxylate and Related Compounds |
| title_full_unstemmed | Methyl 12-Methyl-3,9-dinitro-5,6,7,12-tetrahydro-13-oxodibenzo[<i>b</i>.<i>g</i>]bicyclo[3.3.1]nonane-6-carboxylate and Related Compounds |
| title_short | Methyl 12-Methyl-3,9-dinitro-5,6,7,12-tetrahydro-13-oxodibenzo[<i>b</i>.<i>g</i>]bicyclo[3.3.1]nonane-6-carboxylate and Related Compounds |
| title_sort | methyl 12 methyl 3 9 dinitro 5 6 7 12 tetrahydro 13 oxodibenzo i b i i g i bicyclo 3 3 1 nonane 6 carboxylate and related compounds |
| topic | double alkylation double S<sub>N</sub>Ar ring closure dibenzo[3.3.1]bicyclic systems |
| url | https://www.mdpi.com/1422-8599/2022/4/M1526 |
| work_keys_str_mv | AT dylanrnanney methyl12methyl39dinitro56712tetrahydro13oxodibenzoibiigibicyclo331nonane6carboxylateandrelatedcompounds AT richardabunce methyl12methyl39dinitro56712tetrahydro13oxodibenzoibiigibicyclo331nonane6carboxylateandrelatedcompounds |