A New Class of Enehydroxylamino Ketones − (R)-2-(1-Hydroxy-4,4,5,5-tetraalkylimidazolidin-2-ylidene)ethanones: Synthesis and Reactions
Three approaches to the synthesis of (R)‐2‐(1‐hydroxy‐4,4,5,5‐tetraalkylimidazolidin‐2‐ylidene)ethanones 1 are described: (a) condensation of 1,2‐bishydroxylamines with β‐ketoaldehyde synthons, (b) treatment of metallated 1‐hydroxy‐2‐methyl‐4,5‐dihydroimidazoles with esters, and (c) 1,3‐dipolar cycl...
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| Veröffentlicht in: | European journal of organic chemistry 2004-02, Vol.2004 (4), p.749-765 |
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| container_title | European journal of organic chemistry |
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| creator | Reznikov, Vladimir A. Roshchupkina, Galina I. Mazhukin, Dmitrii G. Petrov, Pavel A. Popov, Sergei A. Fokin, Sergey V. Romanenko, Galina V. Rybalova, Tatjana V. Gatilov, Yuri V. Shvedenkov, Yuri G. Irtegova, Irina G. Shundrin, Leonid A. Ovcharenko, Victor I. |
| description | Three approaches to the synthesis of (R)‐2‐(1‐hydroxy‐4,4,5,5‐tetraalkylimidazolidin‐2‐ylidene)ethanones 1 are described: (a) condensation of 1,2‐bishydroxylamines with β‐ketoaldehyde synthons, (b) treatment of metallated 1‐hydroxy‐2‐methyl‐4,5‐dihydroimidazoles with esters, and (c) 1,3‐dipolar cycloaddition between 1‐hydroxy‐4,5‐dihydroimidazole‐3‐oxide and DMAD. The reactivity of 1 with electrophiles has been studied. The exocyclic methylene (enamine) carbon atom is shown to be the major site of electrophilic attack. Synthesized chloro‐substituted 1‐hydroxy‐2‐acetylideneimidazolidines react with sodium cyanide to form the corresponding nitriles. Oxidation of these nitriles occurs with formation of persistent vinyl nitroxides, which are of interest as potential paramagnetic ligands. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004) |
| doi_str_mv | 10.1002/ejoc.200300536 |
| format | Article |
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The reactivity of 1 with electrophiles has been studied. The exocyclic methylene (enamine) carbon atom is shown to be the major site of electrophilic attack. Synthesized chloro‐substituted 1‐hydroxy‐2‐acetylideneimidazolidines react with sodium cyanide to form the corresponding nitriles. Oxidation of these nitriles occurs with formation of persistent vinyl nitroxides, which are of interest as potential paramagnetic ligands. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.200300536</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Enaminones ; EPR spectroscopy ; Imidazolidines ; Ketones ; Nitroxides ; Nucleophilic substitution</subject><ispartof>European journal of organic chemistry, 2004-02, Vol.2004 (4), p.749-765</ispartof><rights>Copyright © 2004 WILEY‐VCH Verlag GmbH & Co. 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J. Org. Chem</addtitle><description>Three approaches to the synthesis of (R)‐2‐(1‐hydroxy‐4,4,5,5‐tetraalkylimidazolidin‐2‐ylidene)ethanones 1 are described: (a) condensation of 1,2‐bishydroxylamines with β‐ketoaldehyde synthons, (b) treatment of metallated 1‐hydroxy‐2‐methyl‐4,5‐dihydroimidazoles with esters, and (c) 1,3‐dipolar cycloaddition between 1‐hydroxy‐4,5‐dihydroimidazole‐3‐oxide and DMAD. The reactivity of 1 with electrophiles has been studied. The exocyclic methylene (enamine) carbon atom is shown to be the major site of electrophilic attack. Synthesized chloro‐substituted 1‐hydroxy‐2‐acetylideneimidazolidines react with sodium cyanide to form the corresponding nitriles. Oxidation of these nitriles occurs with formation of persistent vinyl nitroxides, which are of interest as potential paramagnetic ligands. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)</description><subject>Enaminones</subject><subject>EPR spectroscopy</subject><subject>Imidazolidines</subject><subject>Ketones</subject><subject>Nitroxides</subject><subject>Nucleophilic substitution</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><recordid>eNqFkE1P20AQhi1UJFLolfMeQcqGWe-H496QlfKVBikFwW21Xs8qC84aeS2B-ws48xP7S-ooKOqtc5nR6H3ew5MkxwwmDCA9w6fGTlIADiC52ktGDPKcgsrhy3ALLijL-eNB8jXGJwDIlWKj5P2cLPCVFLWJkTSOzAKu-qpt3vrarH1oyA12TcBI_rx_kJPlKU3pCaOX2wgVYzGWY0k77Fpj6ue-9mtfmd9N7SsfhuzwqDDgKXYrEzY938mvPnQrjD4SEyqyRGM734R4lOw7U0f89rkPk_sfs7viks5vL66K8zm1PJWKqtRNlYBcMscEYK7cFC0XytnKSgHKWqe4hEyU0pSmdAp5OYwoVSanJRh-mEy2vbZtYmzR6ZfWr03bawZ641FvPOqdxwHIt8Crr7H_T1rPrm-Lf1m6ZX3s8G3HmvZZq4xnUj8sLnQhrpc32U-mH_hfdPqH5w</recordid><startdate>200402</startdate><enddate>200402</enddate><creator>Reznikov, Vladimir A.</creator><creator>Roshchupkina, Galina I.</creator><creator>Mazhukin, Dmitrii G.</creator><creator>Petrov, Pavel A.</creator><creator>Popov, Sergei A.</creator><creator>Fokin, Sergey V.</creator><creator>Romanenko, Galina V.</creator><creator>Rybalova, Tatjana V.</creator><creator>Gatilov, Yuri V.</creator><creator>Shvedenkov, Yuri G.</creator><creator>Irtegova, Irina G.</creator><creator>Shundrin, Leonid A.</creator><creator>Ovcharenko, Victor I.</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>200402</creationdate><title>A New Class of Enehydroxylamino Ketones − (R)-2-(1-Hydroxy-4,4,5,5-tetraalkylimidazolidin-2-ylidene)ethanones: Synthesis and Reactions</title><author>Reznikov, Vladimir A. ; Roshchupkina, Galina I. ; Mazhukin, Dmitrii G. ; Petrov, Pavel A. ; Popov, Sergei A. ; Fokin, Sergey V. ; Romanenko, Galina V. ; Rybalova, Tatjana V. ; Gatilov, Yuri V. ; Shvedenkov, Yuri G. ; Irtegova, Irina G. ; Shundrin, Leonid A. ; Ovcharenko, Victor I.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3256-62f8640951f140e96f8ec346fcdc5406ccf635074b5ababf6e3bbbb4b6758b0a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Enaminones</topic><topic>EPR spectroscopy</topic><topic>Imidazolidines</topic><topic>Ketones</topic><topic>Nitroxides</topic><topic>Nucleophilic substitution</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Reznikov, Vladimir A.</creatorcontrib><creatorcontrib>Roshchupkina, Galina I.</creatorcontrib><creatorcontrib>Mazhukin, Dmitrii G.</creatorcontrib><creatorcontrib>Petrov, Pavel A.</creatorcontrib><creatorcontrib>Popov, Sergei A.</creatorcontrib><creatorcontrib>Fokin, Sergey V.</creatorcontrib><creatorcontrib>Romanenko, Galina V.</creatorcontrib><creatorcontrib>Rybalova, Tatjana V.</creatorcontrib><creatorcontrib>Gatilov, Yuri V.</creatorcontrib><creatorcontrib>Shvedenkov, Yuri G.</creatorcontrib><creatorcontrib>Irtegova, Irina G.</creatorcontrib><creatorcontrib>Shundrin, Leonid A.</creatorcontrib><creatorcontrib>Ovcharenko, Victor I.</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Reznikov, Vladimir A.</au><au>Roshchupkina, Galina I.</au><au>Mazhukin, Dmitrii G.</au><au>Petrov, Pavel A.</au><au>Popov, Sergei A.</au><au>Fokin, Sergey V.</au><au>Romanenko, Galina V.</au><au>Rybalova, Tatjana V.</au><au>Gatilov, Yuri V.</au><au>Shvedenkov, Yuri G.</au><au>Irtegova, Irina G.</au><au>Shundrin, Leonid A.</au><au>Ovcharenko, Victor I.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A New Class of Enehydroxylamino Ketones − (R)-2-(1-Hydroxy-4,4,5,5-tetraalkylimidazolidin-2-ylidene)ethanones: Synthesis and Reactions</atitle><jtitle>European journal of organic chemistry</jtitle><addtitle>Eur. 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| ispartof | European journal of organic chemistry, 2004-02, Vol.2004 (4), p.749-765 |
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| source | Wiley Online Library - AutoHoldings Journals |
| subjects | Enaminones EPR spectroscopy Imidazolidines Ketones Nitroxides Nucleophilic substitution |
| title | A New Class of Enehydroxylamino Ketones − (R)-2-(1-Hydroxy-4,4,5,5-tetraalkylimidazolidin-2-ylidene)ethanones: Synthesis and Reactions |
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