Reaction of Active Methylene Groups with 1,2-Di(Bromoseleno)Benzene toward Benzo-1,3(2H)-Diselenoles
The 1,2-di(bromoseleno)benzene has been found to be a bifunctional electrophile able to react with C-H acids. The tandem diselenylation of the active methylene group in β-diketones, β-keto- and β-cyanoesters, diethyl malonate, and malonitrile resulted in the ring closure on the carbon atom. Based on...
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| Published in | Synthetic communications Vol. 35; no. 8; pp. 1077 - 1083 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
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01.04.2005
Taylor & Francis |
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| Abstract | The 1,2-di(bromoseleno)benzene has been found to be a bifunctional electrophile able to react with C-H acids. The tandem diselenylation of the active methylene group in β-diketones, β-keto- and β-cyanoesters, diethyl malonate, and malonitrile resulted in the ring closure on the carbon atom. Based on this reaction, 2,2-disubstituted benzo-1,3(2H)-diselenoles, a new group of selenaheterocycles, were obtained in good yields. |
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| AbstractList | The 1,2-di(bromoseleno)benzene has been found to be a bifunctional electrophile able to react with C-H acids. The tandem diselenylation of the active methylene group in β-diketones, β-keto- and β-cyanoesters, diethyl malonate, and malonitrile resulted in the ring closure on the carbon atom. Based on this reaction, 2,2-disubstituted benzo-1,3(2H)-diselenoles, a new group of selenaheterocycles, were obtained in good yields. The 1,2-di(bromoseleno)benzene has been found to be a bifunctional electrophile able to react with C-H acids. The tandem diselenylation of the active methylene group in beta-diketones, beta-keto- and beta-cyanoesters, diethyl malonate, and malonitrile resulted in the ring closure on the carbon atom. Based on this reaction, 2,2-disubstituted benzo-1,3(2H)-diselenoles, a new group of selenaheterocycles, were obtained in good yields. |
| Author | Kloc, Krystian Potaczek, Piotr Młochowski, Jacek |
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| Keywords | diethyl malonate 1,3-diketones selenium compounds 1,2-di(bromoseleno)benzene benzo-1,3(2H)-diselenoles SELENIUM |
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| References | Kloc, K (WOS:000077978100009) 1999; 1999 Mugesh, G (WOS:000170045000011) 2001; 101 PROCTER DJ (WOS:000228451200010.12) 2000; 6 Kloc, K (WOS:000186375500019) 2003; 33 Kloc, K (WOS:000175894400026) 2002; 43 Tiecco, M (WOS:000089036200002) 2000; 208 Kloc, K (WOS:000169715900039) 2001; 42 IWAOKA M (WOS:000228451200010.2) 1994; 1 Mugesh, G (WOS:000089142000007) 2000; 29 Mlochowski, J (WOS:A1996VV36000007) 1996 Giurg, M (WOS:000080493700012) 1999; 29 LAMBERT, C (WOS:A1984SE58800011) 1984; 25 PAULMIER C (WOS:000228451200010.11) 1986 Wirth, T (WOS:000077634800001) 1999; 55 Paulmier C. (CIT0001) 1986 Procter D. J. (CIT0004) 2000; 6 Giurg M. (CIT0015) 1999; 29 Kloc K. (CIT0011) 2003; 33 Młochowski J. (CIT0009) 1993; 12 Tiecco M. (CIT0002) 2000; 208 Lambert C. (CIT0016) 1984; 25 Iwaoka M. (CIT0003) 1994; 1 Kloc K. (CIT0012) 1999; 1 Mugesh G. (CIT0006) 2000; 29 Kloc K. (CIT0013) 2001; 42 CIT0014 Młochowski J. (CIT0008) 2003; 22 CIT0005 CIT0007 Młochowski J. (CIT0010) 1996; 11 |
| References_xml | – volume: 43 start-page: 4071 year: 2002 ident: WOS:000175894400026 article-title: New heterocyclic selenenamides: 1,2,4-benzoselenadiazin-3(4H)-ones and 1,3,2-benzodiselenazoles publication-title: TETRAHEDRON LETTERS contributor: fullname: Kloc, K – volume: 29 start-page: 2281 year: 1999 ident: WOS:000080493700012 article-title: Oxidative ring contraction of cycloalkanones: A facile method for synthesis of medium ring cycloalkanecarboxylic acids publication-title: SYNTHETIC COMMUNICATIONS contributor: fullname: Giurg, M – volume: 29 start-page: 347 year: 2000 ident: WOS:000089142000007 article-title: Synthetic organoselenium compounds as antioxidants: glutathione peroxidase activity publication-title: CHEMICAL SOCIETY REVIEWS contributor: fullname: Mugesh, G – year: 1986 ident: WOS:000228451200010.11 publication-title: SELENIUM REAGENTS IN contributor: fullname: PAULMIER C – volume: 25 start-page: 833 year: 1984 ident: WOS:A1984SE58800011 article-title: ALTERNATIVE SYNTHESES OF DIBENZOTETRASELENAFULVALENE, OF SOME OF ITS PRECURSORS AND OF TETRASELENOALKENES ANALOGS publication-title: TETRAHEDRON LETTERS contributor: fullname: LAMBERT, C – volume: 6 start-page: 835 year: 2000 ident: WOS:000228451200010.12 publication-title: J CHEM SOC P1 contributor: fullname: PROCTER DJ – start-page: 1751 year: 1996 ident: WOS:A1996VV36000007 article-title: Synthesis and properties of 2-carboxyalkyl-1,2-benzisoselenazol-3(2H)-ones and related organoselenium compounds as nitric oxide synthase inhibitors and cytokine inducers publication-title: LIEBIGS ANNALEN contributor: fullname: Mlochowski, J – volume: 1999 start-page: 67 year: 1999 ident: WOS:000077978100009 article-title: Synthesis of organoselenium sulfonamides as new potential cytokine inducers: 2,2 '-diselenobis(benzenesulfonamides) and 1,3,2-benzothiaselenazolone 1,1-dioxides publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Kloc, K – volume: 101 start-page: 2125 year: 2001 ident: WOS:000170045000011 article-title: Chemistry of biologically important synthetic organoselenium compounds publication-title: CHEMICAL REVIEWS doi: 10.1021/cr000426w contributor: fullname: Mugesh, G – volume: 55 start-page: 1 year: 1999 ident: WOS:000077634800001 article-title: Chiral selenium compounds in organic synthesis publication-title: TETRAHEDRON contributor: fullname: Wirth, T – volume: 208 start-page: 7 year: 2000 ident: WOS:000089036200002 article-title: Electrophilic selenium, selenocyclizations publication-title: ORGANOSELENIUM CHEMISTRY contributor: fullname: Tiecco, M – volume: 42 start-page: 4899 year: 2001 ident: WOS:000169715900039 article-title: Selenenylation-acylation of ketones with 2-chloroselenobenzoyl chloride. A novel route to benzo[b]selenophenes publication-title: TETRAHEDRON LETTERS contributor: fullname: Kloc, K – volume: 33 start-page: 3805 year: 2003 ident: WOS:000186375500019 article-title: Synthesis of 7-azabenzisoselenazol-3(2,H)-ones: A new group of selenium containing antimicrobials publication-title: SYNTHETIC COMMUNICATIONS doi: 10.1081/SCC-120025191 contributor: fullname: Kloc, K – volume: 1 start-page: 261 year: 1994 ident: WOS:000228451200010.2 publication-title: ENCY REAGENTS ORGANI contributor: fullname: IWAOKA M – volume: 22 start-page: 4329 year: 2003 ident: CIT0008 publication-title: Eur. J. Org. Chem. doi: 10.1002/ejoc.200300230 contributor: fullname: Młochowski J. – volume: 208 start-page: 7 year: 2000 ident: CIT0002 publication-title: Topics Curr. Chem. doi: 10.1007/3-540-48171-0_2 contributor: fullname: Tiecco M. – volume: 12 start-page: 1293 year: 1993 ident: CIT0009 publication-title: Liebigs Ann. 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| Snippet | The 1,2-di(bromoseleno)benzene has been found to be a bifunctional electrophile able to react with C-H acids. The tandem diselenylation of the active methylene... |
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| SubjectTerms | 1,2-di(bromoseleno)benzene 1,3-diketones benzo-1,3(2H)-diselenoles Chemistry Chemistry, Organic diethyl malonate Physical Sciences Science & Technology selenium compounds |
| Title | Reaction of Active Methylene Groups with 1,2-Di(Bromoseleno)Benzene toward Benzo-1,3(2H)-Diselenoles |
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