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...

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Main Authors:	Vahid Ziaee, Hasan Jalalizadeh, Mehrdad Iranshahi, Abbas Shafiee
Format:	Article
Language:	English
Published:	Iranian Institute of Research and Development in Chemical Industries (IRDCI)-ACECR 2004-12-01
Series:	Iranian Journal of Chemistry & Chemical Engineering
Subjects:	vasicinone synthesis monobromodeoxyvasicinone acetylvasicinone
Online Access:	http://www.ijcce.ac.ir/article_8136_5f735c46c0d77073fb31d436c9691f44.pdf

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spelling	doaj-a0b8416d5c154e459bad3b92cd88f4c62020-11-25T01:46:32ZengIranian Institute of Research and Development in Chemical Industries (IRDCI)-ACECRIranian Journal of Chemistry & Chemical Engineering 1021-99861021-99862004-12-0123233368136Improved 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
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Vahid Ziaee Hasan Jalalizadeh Mehrdad Iranshahi Abbas Shafiee
spellingShingle	Vahid Ziaee Hasan Jalalizadeh Mehrdad Iranshahi Abbas Shafiee Improved Synthesis of Vasicinone Iranian Journal of Chemistry & Chemical Engineering vasicinone synthesis monobromodeoxyvasicinone acetylvasicinone
author_facet	Vahid Ziaee Hasan Jalalizadeh Mehrdad Iranshahi Abbas Shafiee
author_sort	Vahid Ziaee
title	Improved Synthesis of Vasicinone
title_short	Improved Synthesis of Vasicinone
title_full	Improved Synthesis of Vasicinone
title_fullStr	Improved Synthesis of Vasicinone
title_full_unstemmed	Improved Synthesis of Vasicinone
title_sort	improved synthesis of vasicinone
publisher	Iranian Institute of Research and Development in Chemical Industries (IRDCI)-ACECR
series	Iranian Journal of Chemistry & Chemical Engineering
issn	1021-9986 1021-9986
publishDate	2004-12-01
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.
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
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Improved Synthesis of Vasicinone

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