Improved Synthesis of Vasicinone
A new, high yielding method for the preparation of vasicinone (7) is described. Reaction of 2-nitrobenzoic acid with N, N¢-carbonyldiimidazole followed by 2-pyrrolidinone gave 1-(2-nitrobenzoyl)pyrrolidine-2-one (3). Reduction of the latter with 10% Pd-C afforded deoxyvasicinone (4). Reaction of deo...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Iranian Institute of Research and Development in Chemical Industries (IRDCI)-ACECR
2004-12-01
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| Series: | Iranian Journal of Chemistry & Chemical Engineering |
| Subjects: | |
| Online Access: | http://www.ijcce.ac.ir/article_8136_5f735c46c0d77073fb31d436c9691f44.pdf |
| _version_ | 1818063166303633408 |
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| author | Vahid Ziaee Hasan Jalalizadeh Mehrdad Iranshahi Abbas Shafiee |
| author_facet | Vahid Ziaee Hasan Jalalizadeh Mehrdad Iranshahi Abbas Shafiee |
| author_sort | Vahid Ziaee |
| collection | DOAJ |
| description | A new, high yielding method for the preparation of vasicinone (7) is described. Reaction of 2-nitrobenzoic acid with N, N¢-carbonyldiimidazole followed by 2-pyrrolidinone gave 1-(2-nitrobenzoyl)pyrrolidine-2-one (3). Reduction of the latter with 10% Pd-C afforded deoxyvasicinone (4). Reaction of deoxyvasicinone (4) with bromine yielded monobromo-deoxyvasicinone (5). Exchange of bromine of 5 with acetoxy followed by hydrolysis gave vasicinone in high yield. |
| first_indexed | 2024-12-10T14:15:47Z |
| format | Article |
| id | doaj.art-a0b8416d5c154e459bad3b92cd88f4c6 |
| institution | Directory Open Access Journal |
| issn | 1021-9986 1021-9986 |
| language | English |
| last_indexed | 2024-12-10T14:15:47Z |
| publishDate | 2004-12-01 |
| publisher | Iranian Institute of Research and Development in Chemical Industries (IRDCI)-ACECR |
| record_format | Article |
| series | Iranian Journal of Chemistry & Chemical Engineering |
| spelling | doaj.art-a0b8416d5c154e459bad3b92cd88f4c62022-12-22T01:45:21ZengIranian Institute of Research and Development in Chemical Industries (IRDCI)-ACECRIranian Journal of Chemistry & Chemical Engineering1021-99861021-99862004-12-0123233368136Improved Synthesis of VasicinoneVahid Ziaee0Hasan Jalalizadeh1Mehrdad Iranshahi2Abbas Shafiee3Department of Medicinal Chemistry and Pharmaceutical Sciences Research Center , Faculty of Pharmacy, Tehran University of Medical Sciences, P.O. Box 14155-6451, Tehran, I.R. IRANDepartment of Medicinal Chemistry and Pharmaceutical Sciences Research Center , Faculty of Pharmacy, Tehran University of Medical Sciences, P.O. Box 14155-6451, Tehran, I.R. IRANDepartment of Medicinal Chemistry and Pharmaceutical Sciences Research Center , Faculty of Pharmacy, Tehran University of Medical Sciences, P.O. Box 14155-6451, Tehran, I.R. IRANDepartment of Medicinal Chemistry and Pharmaceutical Sciences Research Center , Faculty of Pharmacy, Tehran University of Medical Sciences, P.O. Box 14155-6451, Tehran, I.R. IRANA new, high yielding method for the preparation of vasicinone (7) is described. Reaction of 2-nitrobenzoic acid with N, N¢-carbonyldiimidazole followed by 2-pyrrolidinone gave 1-(2-nitrobenzoyl)pyrrolidine-2-one (3). Reduction of the latter with 10% Pd-C afforded deoxyvasicinone (4). Reaction of deoxyvasicinone (4) with bromine yielded monobromo-deoxyvasicinone (5). Exchange of bromine of 5 with acetoxy followed by hydrolysis gave vasicinone in high yield.http://www.ijcce.ac.ir/article_8136_5f735c46c0d77073fb31d436c9691f44.pdfvasicinonesynthesismonobromodeoxyvasicinoneacetylvasicinone |
| spellingShingle | Vahid Ziaee Hasan Jalalizadeh Mehrdad Iranshahi Abbas Shafiee Improved Synthesis of Vasicinone Iranian Journal of Chemistry & Chemical Engineering vasicinone synthesis monobromodeoxyvasicinone acetylvasicinone |
| title | Improved Synthesis of Vasicinone |
| title_full | Improved Synthesis of Vasicinone |
| title_fullStr | Improved Synthesis of Vasicinone |
| title_full_unstemmed | Improved Synthesis of Vasicinone |
| title_short | Improved Synthesis of Vasicinone |
| title_sort | improved synthesis of vasicinone |
| topic | vasicinone synthesis monobromodeoxyvasicinone acetylvasicinone |
| url | http://www.ijcce.ac.ir/article_8136_5f735c46c0d77073fb31d436c9691f44.pdf |
| work_keys_str_mv | AT vahidziaee improvedsynthesisofvasicinone AT hasanjalalizadeh improvedsynthesisofvasicinone AT mehrdadiranshahi improvedsynthesisofvasicinone AT abbasshafiee improvedsynthesisofvasicinone |