Selenium–Nitrogen Bond Cleavage in Selenazole Ring System with Grignard Reagent: A Convenient Synthesis of Unsymmetrically Substituted Selenides

REFERENCES

• Młochowski , J. 1,2-Selenazoles ; In Comprehensive Heterocyclic Chemistry III ; A. R. Katritzky , C. A. Ramsden , E. V. F. Scriven , R. J. K. Taylor (Eds.); Elsevier : Oxford , 2008 ; chap 4.7.
   Google Scholar
• Młochowski , J. ; Giurg , M. Aromaticity of heterocyclic compounds ; In Topics in Heterocyclic Chemistry ; T. Krygowski , M. Cyranski (Eds.); Springer : Heidelberg , 2008 .
   Google Scholar
• Młochowski , J. ; Kloc , K. ; Lisiak , R. ; Potaczek , P. ; Wójtowicz , H. Developments in the chemistry of selenaheterocyclic compounds of practical importance in synthesis and medicinal biology . Arkivoc 2007 , 6 , 14 – 46 .
   Google Scholar
• Młochowski , J. ; Kloc , K. ; Syper , L. ; Inglot , A. ; Piasecki , E. Aromatic and azaaromatic diselenides, benzisoselenazolones, and related compounds as immunomodulators active in humans: Synthesis and properties . Liebigs Ann. Chem. 1993 , 12 , 1239 – 1244 .
   Google Scholar
• Lisiak , R. ; Palus , J. ; Młochowski , J. Nucleophilic cleavage of selenaheterocyclic ring in benzisoselenazol-3(2H)-ones and 1,3,2-benzodiselenazoles . Pol. J. Chem. 2007 , 81 , 1403 – 1413 .
   Google Scholar
• Dallacker , F. ; Peisker , A. Reaktionen an 2-substituierten 1,2-Benzoisoselenazol-3(2H)-onen . Chem. Zeit. 1991 , 115 ( 6 ), 169 – 172 .
   Google Scholar
• (a) Chatgilialoglu , C. ; Guerra , M. ; Guerrini , A. ; Seconi , G. A study on the reducing abilities of tris(alkylthio)silannes . J. Org. Chem. 1992 , 57 ( 8 ), 2427 – 2433 ; (b) Tiecco , M. ; Testaferri , L. ; Temperini , A. ; Terlizzi , R. ; Bagnoli , L. ; Marini , F. ; Santi , C. Synthesis of selenoxides by oxidation of selenides with superoxide radical anions and 2-nitrobenzenesulfonyl chloride . Tetrahedron Lett. 2005 , 46 ( 31 ), 5165 – 5168 .
   Web of Science ®Google Scholar
• Reich , H. J. ; Renga , J. M. ; Reich , I. L. Organoselenium chemistry: Conversion of ketones to enones by selenoxide syn elimination . J. Am. Chem. Soc. 1975 , 97 ( 19 ), 5434 – 5447 .
   Web of Science ®Google Scholar
• Hori , T. ; Sharpless , K. B. Synthetic applications of arylselenenic and arylseleninic acids: Conversion of olefins to allylic alcohols and epoxides . J. Org. Chem. 1978 , 43 ( 9 ), 1689 – 1697 .
   Web of Science ®Google Scholar
• Hyugano , T. ; Liu , S. ; Ouchi , A. Facile photochemical transformation of alkyl aryl selenides to the corresponding carbonyl compounds by molecular oxygen: use of selenides as masked carbonyl groups. J. Org. Chem. 2008, 73 (22), 8861–8866.
   PubMed Web of Science ®Google Scholar
• Takada , H. ; Oda , M. ; Miyake , Y. ; Ohe , K. ; Uemura , S. Catalytic asymmetric imidation of selenides into selenimides . Chem. Commun. 1998 , 1557 – 1558 .
   Web of Science ®Google Scholar
• (a) Krief , A. ; Hevesi , L. In Organoselenium Chemistry ; Springer-Verlag : Berlin , 1988 ; vol. 1 ; (b) Paulmier , C. Selenium Reagents and Intermediates in Organic Synthesis ; Pergamon Press : Oxford , 1986 ; (c) Patai , S. ; Rappoport , Z. In The Chemistry of Organic Selenium and Tellurium Compounds ; Wiley & Sons : New York , 1986 and 1987 ; vols. 1 and 2 ; (d) Krief , A. In Comprehensive Organometallic Chemistry ; B. M. Trost (Eds.); Pergamon Press : Oxford , 1991 ; pp. 85 – 192
   Google Scholar
• Xie , M. H. ; Wu , L. L. ; Huang , X. Stereoselective synthesis of δ-selanyl allylic alcohols by hydrizirconation of propargyl selenides . Chin. Chem. Lett. 2003 , 14 ( 3 ), 255 – 256 .
   Web of Science ®Google Scholar
• Xu , W. M. ; Zhang , Y. C. ; Huang , X. Polystyrene-supported selenides and selenoxide: versatile routes to synthesize allylic alcohols . Chin. Chem. Lett. 2003 , 14 ( 8 ), 797 – 799 .
   Web of Science ®Google Scholar
• (a) Korchevin , N. A. ; Ostroukhova , L. A. ; Ivanova , N. D. ; Deryagina , E. N. ; Voronkov , M. G. Termitheskaia gazophaznaia reakcija iodobenzola s dimetylselenidom i-selenidom . J. Gen. Chem. USSR 1990 , 60 ( 7.2 ), 1495 – 1496 ; (b) Tiecco , M. ; Testaferri , L. ; Tingoli , M. ; Chianelli , D. ; Montanucci , M. Nucleophilic aromatic substitutions of unactivated aryl halides by methyl selenide anions. Synthesis and selective dealkylations of aryl alkyl selenides . J. Org. Chem. 1983 , 48 ( 23 ), 4289 – 4296 .
   Google Scholar
• Nishino , T. ; Okada , M. ; Kuroki , T. ; Watanabe , T. ; Nishiyama , Y. ; Sonoda , N. One-pot synthetic method of unsymmetrical diorganyl selenides: Reaction of diphenyl diselenide with alkyl halides in the presence of lanthanum metal . J. Org. Chem. 2002 , 67 ( 24 ), 8696 – 8698 .
   PubMed Web of Science ®Google Scholar
• Braga , A. L. ; Schneider , P. H. ; Paixau , M. W. ; Deobald , A. M. Efficient synthesis of diorganyl selenides via cleavage of Se-Se bond of diselenides by indium(III) catalyst and zink . Tetrahedron Lett. 2006 , 47 , 7195 – 7198 .
   Web of Science ®Google Scholar
• Taniguchi , N. Convenient synthesis of unsymmetrical organochalcogenides using organoboronic acids with dichalcogenides via cleavage of the S-S, Se–Se, or Te–Te bond by a copper catalyst . J. Org. Chem. 2007 , 72 ( 4 ), 1241 – 1245 .
   PubMed Web of Science ®Google Scholar
• Młochowski , J. ; Gryglewski , R. J. ; Inglot , A. D. ; Jakubowski , A. ; Juchniewicz , L. ; Kloc , K. Synthesis and properties of 2-carboxyalkyl-1,2-benzisoselenazol-3(2H)-ones and related organoselenium compounds as a nitric oxide synthase inhibitors and cytokine inducers . Liebigs Ann. Chem. 1996 , 11 , 1751 – 1755 .
   Google Scholar
• (a) Giurg , M. ; Said , S. B. ; Syper , L. ; Młochowski , J. One-pot oxidation of azomethine compounds into arenecarboxylic acids . Synth. Commun. 2001 , 31 , 3151 – 3159 ; (b) Kloc , K. ; Młochowski , J. ; Osajda , K. ; Syper , L. ; Wójtowicz , H. New heterocyclic selenenamides: 1,2,4-Benzoselenadiazin-3(4H)-ones and 1,3,2-benzodiselenazoles . Tetrahedron Lett. 2002 , 43 , 4071 – 4074 .
   Web of Science ®Google Scholar
• Kloc , K. ; Młochowski , J. Synthesis of organoselenium sulfonamides as new potential cytokine inducers: 2,2′-Diselenobis(benzenosulfonamides) and 1,3,2-benzothiaselenazole 1,1-dioxides. Eur. J. Org. Chem. 1999, 1, 67–71.
   Google Scholar