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Volumn 43, Issue 23, 2013, Pages 3233-3237

Improved method for the iodination of sydnones

Author keywords

Iodination; Mesoionic compounds; Sydnones

Indexed keywords

BENZALKONIUM CHLORIDE; SYDNONE DERIVATIVE;

EID: 84890144465     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2013.779713     Document Type: Article
Times cited : (13)

References (42)
  • 1
    • 71749097873 scopus 로고    scopus 로고
    • Recent developments in the chemistry of sydnones
    • For a comprehensive review of sydnone chemistry, see Browne, D. L.; Harrity, J. P. A. Recent developments in the chemistry of sydnones. Tetrahedron 2010, 66, 553-568.
    • (2010) Tetrahedron , vol.66 , pp. 553-568
    • Browne, D.L.1    Harrity, J.P.A.2
  • 2
    • 84865477858 scopus 로고    scopus 로고
    • Bismuth triflate-catalyzed Friedel-Crafts acylations of sydnones
    • Mahoney, J.; Turnbull, K.; Cubberley, M. Bismuth triflate-catalyzed Friedel-Crafts acylations of sydnones. Synth. Commun. 2012, 42, 3220-3229.
    • (2012) Synth. Commun. , vol.42 , pp. 3220-3229
    • Mahoney, J.1    Turnbull, K.2    Cubberley, M.3
  • 4
    • 0036320830 scopus 로고    scopus 로고
    • The efficient synthesis of new sydnones containing fused ring
    • Zhang, Z. B.; Wu, Y. R.; Yin, C. L. The efficient synthesis of new sydnones containing fused ring. Synth. Commun. 2002, 32, 2203-2207.
    • (2002) Synth. Commun. , vol.32 , pp. 2203-2207
    • Zhang, Z.B.1    Wu, Y.R.2    Yin, C.L.3
  • 5
    • 0031905680 scopus 로고    scopus 로고
    • Direct carboxamidation of sydnones with chlorosulfonyl isocyanate
    • Turnbull, K.; Gross, K. C.; Hall, T. A. Direct carboxamidation of sydnones with chlorosulfonyl isocyanate. Synth. Commun. 1998, 28, 931-937.
    • (1998) Synth. Commun. , vol.28 , pp. 931-937
    • Turnbull, K.1    Gross, K.C.2    Hall, T.A.3
  • 7
    • 0029915618 scopus 로고    scopus 로고
    • Chlorination of 3-substituted sydnones with dichloroiodobenzene
    • Turnbull, K.; Ito, S. Chlorination of 3-substituted sydnones with dichloroiodobenzene. Synth. Commun. 1996, 26, 1441-1446.
    • (1996) Synth. Commun. , vol.26 , pp. 1441-1446
    • Turnbull, K.1    Ito, S.2
  • 8
    • 84993660222 scopus 로고
    • Reactions of activated aryl sydnones with electrophiles
    • Turnbull, K.; Blackburn, T. L.; McClure, D. B. Reactions of activated aryl sydnones with electrophiles. J. Heterocycl. Chem. 1994, 31, 1631-1636.
    • (1994) J. Heterocycl. Chem. , vol.31 , pp. 1631-1636
    • Turnbull, K.1    Blackburn, T.L.2    McClure, D.B.3
  • 9
    • 84986516369 scopus 로고
    • Acetylation and debromination of sydnones accelerated by ultrasound
    • Tien, H.-J.; Yeh, J.-C.; Wu, S.-J. Acetylation and debromination of sydnones accelerated by ultrasound. J. Chin. Chem. Soc. 1992, 39, 443-447.
    • (1992) J. Chin. Chem. Soc. , vol.39 , pp. 443-447
    • Tien, H.-J.1    Yeh, J.-C.2    Wu, S.-J.3
  • 10
    • 84986463145 scopus 로고
    • Bromination of sydnones, III: Bromination of 3-(2-substituted phenyl)-sydnones and subsequent side chain modification
    • Turnbull, K.; Blackburn, T. L.; Esterline, D. T. Bromination of sydnones, III: Bromination of 3-(2-substituted phenyl)-sydnones and subsequent side chain modification. J. Heterocycl. Chem. 1990, 27, 1259-1263.
    • (1990) J. Heterocycl. Chem. , vol.27 , pp. 1259-1263
    • Turnbull, K.1    Blackburn, T.L.2    Esterline, D.T.3
  • 11
    • 84986532525 scopus 로고
    • Bromination of sydnones, I: Reaction with 3-arylsydnones containing electron donors on the aryl ring
    • Turnbull, K. Bromination of sydnones, I: Reaction with 3-arylsydnones containing electron donors on the aryl ring. J. Heterocycl. Chem. 1985, 22, 965-968.
    • (1985) J. Heterocycl. Chem. , vol.22 , pp. 965-968
    • Turnbull, K.1
  • 12
    • 84986517322 scopus 로고
    • Bromination of sydnones, II: Bromination of 3-(2-aminophenyl)sydnone and related compounds
    • Hodson, S. J.; Turnbull, K. Bromination of sydnones, II: Bromination of 3-(2-aminophenyl)sydnone and related compounds. J. Heterocycl. Chem. 1985, 22, 1223-1227.
    • (1985) J. Heterocycl. Chem. , vol.22 , pp. 1223-1227
    • Hodson, S.J.1    Turnbull, K.2
  • 13
    • 33847259169 scopus 로고    scopus 로고
    • 4-Substituted ortho-(silylated phenyl)sydnones via a lithiation-induced silicon migration and subsequent reaction with electrophiles
    • Turnbull, K.; Nashashibi, I. F. 4-Substituted ortho-(silylated phenyl)sydnones via a lithiation-induced silicon migration and subsequent reaction with electrophiles. Synth. Commun. 2007, 37, 915-919.
    • (2007) Synth. Commun. , vol.37 , pp. 915-919
    • Turnbull, K.1    Nashashibi, I.F.2
  • 14
    • 0037715239 scopus 로고    scopus 로고
    • Ortho-(Substituted silyl)phenylsydnones via a novel sydnone to phenyl ring, lithiation-induced silicon migration
    • Turnbull, K.; Krein, D. M. ortho-(Substituted silyl)phenylsydnones via a novel sydnone to phenyl ring, lithiation-induced silicon migration. Synth. Commun. 2003, 33, 2061-2067.
    • (2003) Synth. Commun. , vol.33 , pp. 2061-2067
    • Turnbull, K.1    Krein, D.M.2
  • 15
    • 0032546336 scopus 로고    scopus 로고
    • The sydnone ring as an ortho-director of lithiation, 2: Dilithiation of 3-phenylsydnone and regiospecific o-aryl acylation using N-methoxy-N- methylamides
    • Turnbull, K.; Sun, C.; Krein, D. M. The sydnone ring as an ortho-director of lithiation, 2: Dilithiation of 3-phenylsydnone and regiospecific o-aryl acylation using N-methoxy-N-methylamides. Tetrahedron Lett. 1998, 39, 1509-1512.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 1509-1512
    • Turnbull, K.1    Sun, C.2    Krein, D.M.3
  • 16
    • 0031575647 scopus 로고    scopus 로고
    • The sydnone ring as an ortho-director of lithiation: Dilithiation of 3-phenylsydnone and trapping by electrophiles
    • Turnbull, K.; Krein, D. M. The sydnone ring as an ortho-director of lithiation: Dilithiation of 3-phenylsydnone and trapping by electrophiles. Tetrahedron Lett. 1997, 38, 1165-1168.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 1165-1168
    • Turnbull, K.1    Krein, D.M.2
  • 17
    • 0029812162 scopus 로고    scopus 로고
    • Formation of 4-hydroxy-4-substituted sydno[3,4-A](4H)indoles via dilithiation of 3-(2-bromophenyl)sydnone
    • Turnbull, K.; Krein, D. M. Formation of 4-hydroxy-4-substituted sydno[3,4-a](4H)indoles via dilithiation of 3-(2-bromophenyl)sydnone. Synthesis 1996, 1183-1184.
    • (1996) Synthesis , pp. 1183-1184
    • Turnbull, K.1    Krein, D.M.2
  • 18
    • 0003748314 scopus 로고
    • Synthesis of aryl- and vinylsydnones: Cross-coupling of 4-copper-3-phenylsydnone with aryl and vinyl halides catalyzed by palladium complexes
    • Kalinin, V. N.; Min, S. F. Synthesis of aryl- and vinylsydnones: Cross-coupling of 4-copper-3-phenylsydnone with aryl and vinyl halides catalyzed by palladium complexes. J. Organomet. Chem. 1988, 352, C34-36.
    • (1988) J. Organomet. Chem. , vol.352
    • Kalinin, V.N.1    Min, S.F.2
  • 19
    • 0000003942 scopus 로고
    • Preparation of sydnone compounds substituted by thio and seleno functional groups at the 4-positions
    • Fuchigami, T.; Chen, C.-S.; Nonaka, T.; Yeh, M.-Y.; Tien, H.-J. Preparation of sydnone compounds substituted by thio and seleno functional groups at the 4-positions. Bull. Chem. Soc. Jpn. 1986, 59, 487-491.
    • (1986) Bull. Chem. Soc. Jpn. , vol.59 , pp. 487-491
    • Fuchigami, T.1    Chen, C.-S.2    Nonaka, T.3    Yeh, M.-Y.4    Tien, H.-J.5
  • 21
    • 0000496897 scopus 로고
    • Mesoionic compounds VI: Metalation of sydnones: An estimate of acidity
    • Greco, C. V.; O-Reilly, B. P. Mesoionic compounds VI: Metalation of sydnones: An estimate of acidity. J. Heterocycl. Chem. 1970, 7, 1433-1434.
    • (1970) J. Heterocycl. Chem. , vol.7 , pp. 1433-1434
    • Greco, C.V.1    O-Reilly, B.P.2
  • 22
    • 80055071245 scopus 로고    scopus 로고
    • Synthesis of 2H-indazoles by the [3-2] dipolar cycloaddition of sydnones with arynes
    • Fang, Y.; Wu, C.; Larock, R. C.; Shi, F. Synthesis of 2H-indazoles by the [3-2] dipolar cycloaddition of sydnones with arynes. J. Org. Chem. 2011, 76, 8840-8851.
    • (2011) J. Org. Chem. , vol.76 , pp. 8840-8851
    • Fang, Y.1    Wu, C.2    Larock, R.C.3    Shi, F.4
  • 23
    • 75749084018 scopus 로고    scopus 로고
    • Alkyne [3-2] cycloadditions of iodosydnones toward functionalized 1,3,5-trisubstituted pyrazoles
    • Browne, D. L.; Taylor, J. B.; Plant, A.; Harrity, J. P. A. Alkyne [3-2] cycloadditions of iodosydnones toward functionalized 1,3,5-trisubstituted pyrazoles. J. Org. Chem. 2010, 75, 984-987.
    • (2010) J. Org. Chem. , vol.75 , pp. 984-987
    • Browne, D.L.1    Taylor, J.B.2    Plant, A.3    Harrity, J.P.A.4
  • 24
    • 77955156824 scopus 로고    scopus 로고
    • A modular sydnone cycloaddition=Suzuki-Miyaura cross-coupling strategy to unsymmetrical 3,5-bis(hetero)aromatic pyrazoles
    • Delaunay, T.; Pierre, G.; Mazen, E.-S.; Jean-Pierre, V.; Nuno, M.; Genevieve, B. A modular sydnone cycloaddition=Suzuki-Miyaura cross-coupling strategy to unsymmetrical 3,5-bis(hetero)aromatic pyrazoles. Org. Lett. 2010, 12, 3328
    • (2010) Org. Lett. , vol.12 , pp. 3328-3331
    • Delaunay, T.1    Pierre, G.2    Mazen, E.-S.3    Jean-Pierre, V.4    Nuno, M.5    Genevieve, B.6
  • 25
    • 67650555655 scopus 로고    scopus 로고
    • Investigation of the scope and regiochemistry of alkynylboronate cycloadditions with sydnones
    • Browne, D. L.; Vivat, J. F.; Plant, A.; Gomez-Bengoa, E.; Harrity, J. P. A. Investigation of the scope and regiochemistry of alkynylboronate cycloadditions with sydnones. J. Am. Chem. Soc. 2009, 131, 7762-7769.
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 7762-7769
    • Browne, D.L.1    Vivat, J.F.2    Plant, A.3    Gomez-Bengoa, E.4    Harrity, J.P.A.5
  • 26
    • 53849101867 scopus 로고    scopus 로고
    • 1,3-Dipolar cycloadditions of acetylenic sulfones in solution and on solid supports
    • Gao, D.; Zhai, H.; Parvez, M.; Back, T. G. 1,3-Dipolar cycloadditions of acetylenic sulfones in solution and on solid supports. J. Org. Chem. 2008, 73, 8057-8068.
    • (2008) J. Org. Chem. , vol.73 , pp. 8057-8068
    • Gao, D.1    Zhai, H.2    Parvez, M.3    Back, T.G.4
  • 27
    • 36549038099 scopus 로고    scopus 로고
    • 1,3-Dipolar cycloadditions of silicon and tin alkynes and alkenes: Regiospecific synthesis of silyl and stannylpyrazoles and pyrazolines
    • Gonzalez-Nogal, A. M.; Calle, M.; Cuadrado, P.; Valero, R. 1,3-Dipolar cycloadditions of silicon and tin alkynes and alkenes: Regiospecific synthesis of silyl and stannylpyrazoles and pyrazolines. Tetrahedron 2007, 63, 224-231.
    • (2007) Tetrahedron , vol.63 , pp. 224-231
    • Gonzalez-Nogal, A.M.1    Calle, M.2    Cuadrado, P.3    Valero, R.4
  • 28
    • 37049104771 scopus 로고
    • 1,3-Dipolar cycloadditions with alkynyl phenyl sulphones
    • Croce, P. D.; La Rosa, C.; Zecchi, G. 1,3-Dipolar cycloadditions with alkynyl phenyl sulphones. J. Chem. Soc., Perkin Trans. 1 1985, 2621-2624.
    • (1985) J. Chem. Soc., Perkin Trans. , vol.1 , pp. 2621-2624
    • Croce, P.D.1    La Rosa, C.2    Zecchi, G.3
  • 29
    • 0000233064 scopus 로고
    • On the problem of regioselectivity in the 1,3-dipolar cycloaddition reaction of munchnones and sydnones with acetylenic dipolarophiles
    • Padwa, A.; Burgess, E. M.; Gingrich, H. L.; Roush, D. M. On the problem of regioselectivity in the 1,3-dipolar cycloaddition reaction of munchnones and sydnones with acetylenic dipolarophiles. J. Org. Chem. 1982, 47, 786-791.
    • (1982) J. Org. Chem. , vol.47 , pp. 786-791
    • Padwa, A.1    Burgess, E.M.2    Gingrich, H.L.3    Roush, D.M.4
  • 30
    • 34249812057 scopus 로고    scopus 로고
    • Synthesis of 4-(5-aryl-1,3,4-oxadiazol-2-yl)phenyl-hydrazine derivatives from 3-(4-hydrazinocarbonyl-phenyl)sydnones
    • Chang, H.-T.; Chiang, K.-C.; Wong, F. F.; Huang, C.-S.; Liao, Y.-M.; Kuo, W-F.; Won, S.-B.; Yeh, Y. Synthesis of 4-(5-aryl-1,3,4-oxadiazol-2-yl)phenyl- hydrazine derivatives from 3-(4-hydrazinocarbonyl-phenyl)sydnones. Heteroatom Chem. 1997, 18, 438-442.
    • (1997) Heteroatom Chem. , vol.18 , pp. 438-442
    • Chang, H.-T.1    Chiang, K.-C.2    Wong, F.F.3    Huang, C.-S.4    Liao, Y.-M.5    Kuo, W.-F.6    Won, S.-B.7    Yeh, Y.8
  • 31
    • 0000065008 scopus 로고
    • Acid-induced reactions of a sydnone ketoxime
    • Saljoughian, M.; Turnbull, K. Acid-induced reactions of a sydnone ketoxime. J. Heterocycl. Chem. 1988, 25, 1817-1819.
    • (1988) J. Heterocycl. Chem. , vol.25 , pp. 1817-1819
    • Saljoughian, M.1    Turnbull, K.2
  • 32
    • 49849122106 scopus 로고
    • Hydrolysis of some 3-alkylsydnones
    • Aziz, S.; Tillett, J. G. Hydrolysis of some 3-alkylsydnones. Tetrahedron Lett. 1969, 33, 2855-2858.
    • (1969) Tetrahedron Lett. , vol.33 , pp. 2855-2858
    • Aziz, S.1    Tillett, J.G.2
  • 34
    • 37049155439 scopus 로고
    • Cyclic mesoionic compounds, I: The structure of the sydnones and related compounds
    • Baker, W.; Ollis, W. D.; Poole, V. D. Cyclic mesoionic compounds, I: The structure of the sydnones and related compounds. J. Chem. Soc. 1949, 307-314.
    • (1949) J. Chem. Soc. , pp. 307-314
    • Baker, W.1    Ollis, W.D.2    Poole, V.D.3
  • 35
    • 0027532934 scopus 로고
    • Formation of 1-bromocarbonylindazoles via cleavage of 4-bromo ortho-substituted arylsydnones with HBr
    • Marx, J. A.; Turnbull, K. Formation of 1-bromocarbonylindazoles via cleavage of 4-bromo ortho-substituted arylsydnones with HBr. Tetrahedron Lett. 1993, 34, 239-241
    • (1993) Tetrahedron Lett. , vol.34 , pp. 239-241
    • Marx, J.A.1    Turnbull, K.2
  • 36
    • 0001098630 scopus 로고
    • Sydnones as masked hydrazines for heterocycle formation: Reactions of 3-(2-substituted phenyl)sydnones with HCl
    • Gelvin, C. R.; Turnbull, K. Sydnones as masked hydrazines for heterocycle formation: Reactions of 3-(2-substituted phenyl)sydnones with HCl. Helv. Chim. Acta 1992, 75, 1931-1943.
    • (1992) Helv. Chim. Acta , vol.75 , pp. 1931-1943
    • Gelvin, C.R.1    Turnbull, K.2
  • 37
    • 0007237854 scopus 로고
    • Mesoionic compounds II: Mercuration of 3-phenylsydnone
    • Nakahara, K.; Kato, H. Mesoionic compounds II: Mercuration of 3-phenylsydnone. Nippon Kagaku Zasshi. 1956, 77, 1306-1308.
    • (1956) Nippon Kagaku Zasshi. , vol.77 , pp. 1306-1308
    • Nakahara, K.1    Kato, H.2
  • 38
    • 33749005549 scopus 로고
    • Studies on mesoionic compounds, VII: Reactivities of 4-halosydnones and the reactions of their Grignard reagent
    • Ohta, M.; Kato, H. Studies on mesoionic compounds, VII: Reactivities of 4-halosydnones and the reactions of their Grignard reagent. Nippon Kagaku Zasshi. 1957, 78, 1653-1656.
    • (1957) Nippon Kagaku Zasshi. , vol.78 , pp. 1653-1656
    • Ohta, M.1    Kato, H.2
  • 39
    • 33748989151 scopus 로고
    • Mesoionic compounds, XI: Photochromic 4-halogeno-3-(3-pyridyl)sydnones
    • Greco, C. V.; Mehta, J. R. Mesoionic compounds, XI: Photochromic 4-halogeno-3-(3-pyridyl)sydnones. J. Heterocycl. Chem. 1979, 16, 1059-1060.
    • (1979) J. Heterocycl. Chem. , vol.16 , pp. 1059-1060
    • Greco, C.V.1    Mehta, J.R.2
  • 40
    • 15244348940 scopus 로고    scopus 로고
    • Routes to sydnone-containing oligomeric areneynes
    • Weisner, A. J.; Cooper, T. M.; Turnbull, K. Routes to sydnone-containing oligomeric areneynes. Synth. Commun. 2005, 35, 639-651.
    • (2005) Synth. Commun. , vol.35 , pp. 639-651
    • Weisner, A.J.1    Cooper, T.M.2    Turnbull, K.3
  • 41
    • 0343167660 scopus 로고
    • 3-Phenylsydnone
    • Baumgarten, H. E. 3-Phenylsydnone. Org. Synth. 1973, 5, 962-965
    • (1973) Org. Synth. , vol.5 , pp. 962-965
    • Baumgarten, H.E.1
  • 42
    • 33646378335 scopus 로고
    • Periselective addition of mesoionic compounds to tetracyanoethylene: Preparation of [(dicyanovinyl)hydrazono]-malononitriles
    • Berk, H. C.; Franz, J. E. Periselective addition of mesoionic compounds to tetracyanoethylene: Preparation of [(dicyanovinyl)hydrazono]-malononitriles. J. Org. Chem. 1979, 44, 2395-2400.
    • (1979) J. Org. Chem. , vol.44 , pp. 2395-2400
    • Berk, H.C.1    Franz, J.E.2


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