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Volumn 20, Issue 12, 2015, Pages 22351-22363

Synthesis of New 2-Halo-2-(1H-tetrazol-5-yl)-2H-azirines via a Non-Classical Wittig Reaction

Author keywords

2 halo 2H azirines; Phosphorus ylides; Tetrasubstituted alkenes; Vinyl tetrazoles

Indexed keywords

1H-TETRAZOLE; AZIRINE DERIVATIVE; TETRAZOLE DERIVATIVE;

EID: 84954357488     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules201219848     Document Type: Article
Times cited : (17)

References (38)
  • 1
    • 84875215835 scopus 로고    scopus 로고
    • Recent advances in 2H-azirine chemistry
    • Khlebnikov, A.F.; Novikov, M.S. Recent advances in 2H-azirine chemistry. Tetrahedron 2013, 69, 3363-3401.
    • (2013) Tetrahedron , vol.69 , pp. 3363-3401
    • Khlebnikov, A.F.1    Novikov, M.S.2
  • 2
    • 85021771691 scopus 로고    scopus 로고
    • Ring expansions of azirines and azetines
    • Maes, B.U.W., Cossy, J., Slovenko, P., eds.; Springer Berlin Heidelberg: Berlin, Germany
    • Khlebnikov, A.F.; Novikov, M.S. Ring expansions of azirines and azetines. In Topics in Heterocylicic Chemistry; Maes, B.U.W., Cossy, J., Slovenko, P., eds.; Springer Berlin Heidelberg: Berlin, Germany, 2015; pp. 1-90.
    • (2015) Topics in Heterocylicic Chemistry , pp. 1-90
    • Khlebnikov, A.F.1    Novikov, M.S.2
  • 5
    • 84863293105 scopus 로고    scopus 로고
    • Cycloaddition and cyclization chemistry of 2H-azirines
    • Katritzky, A.R., Ed.; Elsevier Ltd.: Amsterdam, The Netherlands
    • Padwa, A. Cycloaddition and cyclization chemistry of 2H-azirines. In Advances in Heterocyclic Chemistry; Katritzky, A.R., Ed.; Elsevier Ltd.: Amsterdam, The Netherlands, 2010; Volume 99, pp. 1-31.
    • (2010) Advances in Heterocyclic Chemistry , vol.99 , pp. 1-31
    • Padwa, A.1
  • 6
    • 84906433763 scopus 로고    scopus 로고
    • Aziridines and azirines: Monocyclic
    • Katritzky, A.R., Ed.; Elsevier Ltd.: Amsterdam, The Netherlands
    • Padwa, A. Aziridines and azirines: Monocyclic. In Comprehensive Heterocyclic Chemistry III; Katritzky, A.R., Ed.; Elsevier Ltd.: Amsterdam, The Netherlands, 2008; Volume 1, pp. 1-104.
    • (2008) Comprehensive Heterocyclic Chemistry III , vol.1 , pp. 1-104
    • Padwa, A.1
  • 7
    • 0002797864 scopus 로고    scopus 로고
    • The reaction of an α-oxophosphonium ylide with halogens: 2,3-disubstituted diethyl butenedioates from diethyl 2-oxo-3-triphenylphosphoranylidenebutanedioate
    • Gonsalves, A.M.d'A.R.; Cabral, A.M.T.D.P.V.; Pinho e Melo, T.M.V.D.; Gilchrist, T.L. The reaction of an α-oxophosphonium ylide with halogens: 2,3-Disubstituted diethyl butenedioates from diethyl 2-oxo-3-triphenylphosphoranylidenebutanedioate. Synthesis 1997, 673-676.
    • (1997) Synthesis , pp. 673-676
    • Gonsalves A.M.D', A.R.1    Cabral, A.M.T.D.P.V.2    Pinho E Melo, T.M.V.D.3    Gilchrist, T.L.4
  • 9
  • 11
    • 31644443872 scopus 로고    scopus 로고
    • Reactions of unsaturated azides, part 17: An efficient strategy for the synthesis of small-ring heterocycles via isomerization of 2-halo-2H-azirines
    • Fotsing, J.R.; Banert, K. Reactions of unsaturated azides, part 17: An efficient strategy for the synthesis of small-ring heterocycles via isomerization of 2-halo-2H-azirines. Synthesis 2006, 261-272.
    • (2006) Synthesis , pp. 261-272
    • Fotsing, J.R.1    Banert, K.2
  • 12
    • 34548424858 scopus 로고    scopus 로고
    • Alkoxyl radical fragmentation of 3-azido-2,3-dideoxy-2-halo-hexopyranoses: A new entry to chiral polyhydroxylated 2-azido-1-halo-1-alkenes
    • Alonso-Cruz, C.R.; Kennedy, A.R.; Rodríguez, M.S.; Suárez, E. Alkoxyl radical fragmentation of 3-azido-2,3-dideoxy-2-halo-hexopyranoses: A new entry to chiral polyhydroxylated 2-azido-1-halo-1-alkenes. Tetrahedron Lett. 2007, 48, 7207-7210.
    • (2007) Tetrahedron Lett. , vol.48 , pp. 7207-7210
    • Alonso-Cruz, C.R.1    Kennedy, A.R.2    Rodríguez, M.S.3    Suárez, E.4
  • 13
    • 44949255060 scopus 로고    scopus 로고
    • Synthesis of polyhydroxylated 2H-azirines and 2-halo-2H-azirines from 3-azido-2,3-dideoxyhexopyranoses by alkoxyl radical fragmentation
    • Alonso-Cruz, C.R.; Kennedy, A.R.; Rodríguez, M.S.; Suárez, E. Synthesis of polyhydroxylated 2H-azirines and 2-halo-2H-azirines from 3-azido-2,3-dideoxyhexopyranoses by alkoxyl radical fragmentation. Eur. J. Org. Chem. 2008, 73, 4116-4122.
    • (2008) Eur. J. Org. Chem. , vol.73 , pp. 4116-4122
    • Alonso-Cruz, C.R.1    Kennedy, A.R.2    Rodríguez, M.S.3    Suárez, E.4
  • 14
    • 77953191950 scopus 로고    scopus 로고
    • Elusive ethynyl azides: Trapping by 1,3-dipolar cycloaddition and decomposition to cyanocarbenes
    • Banert, K.; Hagedorn, M.; Wutke, J.; Ecochard, P.; Schaarschmidt, D.; Lang, H. Elusive ethynyl azides: Trapping by 1,3-dipolar cycloaddition and decomposition to cyanocarbenes. Chem. Commun. 2010, 46.
    • (2010) Chem. Commun. , pp. 46
    • Banert, K.1    Hagedorn, M.2    Wutke, J.3    Ecochard, P.4    Schaarschmidt, D.5    Lang, H.6
  • 16
    • 33748370971 scopus 로고    scopus 로고
    • New way to methylene-2H-azirines and their use as powerful intermediates for the stereo- and regioselective synthesis of compounds with vinylamine substructure
    • Fotsing, J.R.; Banert, K. New way to methylene-2H-azirines and their use as powerful intermediates for the stereo- and regioselective synthesis of compounds with vinylamine substructure. Eur. J. Org. Chem. 2006, 3617-3625.
    • (2006) Eur. J. Org. Chem. , pp. 3617-3625
    • Fotsing, J.R.1    Banert, K.2
  • 17
    • 58849153578 scopus 로고    scopus 로고
    • 4-halo-1,3-oxazoles: Unambiguous structural assignment of 2-halo-2-benzoyl-2H-azirine-3-carboxylates thermal ring expansion products
    • Lopes, S.; Nunes, C.M.; Fausto, R.; Pinho e Melo, T.M.V.D. 4-Halo-1,3-oxazoles: Unambiguous structural assignment of 2-halo-2-benzoyl-2H-azirine-3-carboxylates thermal ring expansion products. J. Mol. Struct. 2009, 919, 47-53.
    • (2009) J. Mol. Struct. , vol.919 , pp. 47-53
    • Lopes, S.1    Nunes, C.M.2    Fausto, R.3    Pinho E Melo, T.M.V.D.4
  • 18
    • 84871872074 scopus 로고    scopus 로고
    • Thermal rearrangement of azido ketones into oxazoles via azirines: One-pot, metal-free heteroannulation to functionalized 1,3-oxazoles
    • Shah, S.R.; Navathe, S.S.; Dikundwar, A.G.; Row, T.N.G.; Vasella, A.T. Thermal rearrangement of azido ketones into oxazoles via azirines: One-pot, metal-free heteroannulation to functionalized 1,3-oxazoles. Eur. J. Org. Chem. 2013, 264-267.
    • (2013) Eur. J. Org. Chem. , pp. 264-267
    • Shah, S.R.1    Navathe, S.S.2    Dikundwar, A.G.3    Row, T.N.G.4    Vasella, A.T.5
  • 19
    • 84866386080 scopus 로고    scopus 로고
    • Synthesis of electron-poor 4-halo-2-azabuta-1,3-dienes by rh(II)-catalyzed diazo ester-azirine coupling. 2-azabuta-1,3-diene-2,3-dihydroazete valence isomerism
    • Novikov, M.S.; Smetanin, I.A.; Khlebnikov, A.F.; Rostovskii, N.V.; Yufit, D.S. Synthesis of electron-poor 4-halo-2-azabuta-1,3-dienes by Rh(II)-catalyzed diazo ester-azirine coupling. 2-Azabuta-1,3-diene-2,3-dihydroazete valence isomerism. Tetrahedron Lett. 2012, 53, 5777-5780.
    • (2012) Tetrahedron Lett. , vol.53 , pp. 5777-5780
    • Novikov, M.S.1    Smetanin, I.A.2    Khlebnikov, A.F.3    Rostovskii, N.V.4    Yufit, D.S.5
  • 20
    • 84930278447 scopus 로고    scopus 로고
    • 4-halo-2-azabuta-1,3-dienes as intermediates in the rhodium carbenoid-initiated transformation of 2-halo-2H-azirines into 2,3-dihydroazetes and 2,5-dihydrooxazoles
    • Smetanin, I.A.; Novikov, M.S.; Rostovskii, N.V.; Khlebnikov, A.F.; Starova, G.L.; Yufit, D.S. 4-Halo-2-azabuta-1,3-dienes as Intermediates in the rhodium carbenoid-initiated transformation of 2-halo-2H-azirines into 2,3-dihydroazetes and 2,5-dihydrooxazoles. Tetrahedron 2015, 71, 4616-4628.
    • (2015) Tetrahedron , vol.71 , pp. 4616-4628
    • Smetanin, I.A.1    Novikov, M.S.2    Rostovskii, N.V.3    Khlebnikov, A.F.4    Starova, G.L.5    Yufit, D.S.6
  • 22
    • 84905970205 scopus 로고    scopus 로고
    • Selective synthesis of tetrasubstituted 4-(tetrazol-5-yl)-1H-imidazoles from 2-(tetrazol-5-yl)-2H-azirines
    • Cardoso, A.L.; Lemos, A.; Pinho e Melo, T.M.V.D. Selective synthesis of tetrasubstituted 4-(tetrazol-5-yl)-1H-imidazoles from 2-(tetrazol-5-yl)-2H-azirines. Eur. J. Org. Chem. 2014, 24, 5159-5165.
    • (2014) Eur. J. Org. Chem. , vol.24 , pp. 5159-5165
    • Cardoso, A.L.1    Lemos, A.2    Pinho E Melo, T.M.V.D.3
  • 23
    • 0003830553 scopus 로고
    • Haloalkyltetrazole and aminoalkyltetrazole derivatives
    • Harvill, E.K.; Herbst, R.M.; Schreiner, E.G. Haloalkyltetrazole and aminoalkyltetrazole derivatives. J. Org. Chem. 1952, 17, 1597-1616.
    • (1952) J. Org. Chem. , vol.17 , pp. 1597-1616
    • Harvill, E.K.1    Herbst, R.M.2    Schreiner, E.G.3
  • 24
    • 0024562829 scopus 로고
    • Studies on gastric antiulcer active agents. II. Synthesis of tetrazole alkanamides and related compounds
    • Uchida, M.; Komatsu, M.; Morita, S.; Kanbe, T.; Nakagawa, K. Studies on gastric antiulcer active agents. II. Synthesis of tetrazole alkanamides and related compounds. Chem. Pharm. Bull. 1989, 37, 322-326.
    • (1989) Chem. Pharm. Bull. , vol.37 , pp. 322-326
    • Uchida, M.1    Komatsu, M.2    Morita, S.3    Kanbe, T.4    Nakagawa, K.5
  • 26
    • 84883512591 scopus 로고    scopus 로고
    • Synthesis of new tetrazol-5-ylalkenyl derivatives of ferrocene by wittig olefination
    • Grodner, J.; Salaciński, T. Synthesis of new tetrazol-5-ylalkenyl derivatives of ferrocene by wittig olefination. Synthesis 2012, 44, 3071-3076.
    • (2012) Synthesis , vol.44 , pp. 3071-3076
    • Grodner, J.1    Salaciński, T.2
  • 27
    • 33947479967 scopus 로고
    • The preparation and reaction of some halophosphoranes
    • Denney, D.B.; Ross, S.T. The preparation and reaction of some halophosphoranes. J. Org. Chem. 1962, 27, 998-1000.
    • (1962) J. Org. Chem. , vol.27 , pp. 998-1000
    • Denney, D.B.1    Ross, S.T.2
  • 28
    • 0003178779 scopus 로고
    • Halogenation of keto acid phosphoranes: Synthesis of halo enol lactones and haloallenes
    • Abell, A.D.; Murphy, P.J.; Hoult, D.A.; Morris, K.M.; Taylor, J.M.; Trent, J.O. Halogenation of keto acid phosphoranes: Synthesis of halo enol lactones and haloallenes. J. Org. Chem. 1993, 58, 1531-1537.
    • (1993) J. Org. Chem. , vol.58 , pp. 1531-1537
    • Abell, A.D.1    Murphy, P.J.2    Hoult, D.A.3    Morris, K.M.4    Taylor, J.M.5    Trent, J.O.6
  • 29
    • 0027509003 scopus 로고
    • Synthesis of cyclic acylated enamino ester dipeptide analogues via the bromolactonization of a keto acid phosphorane
    • Abell, A.D.; Taylor, J.M. Synthesis of cyclic acylated enamino ester dipeptide analogues via the bromolactonization of a keto acid phosphorane. J. Org. Chem. 1993, 58, 14-15.
    • (1993) J. Org. Chem. , vol.58 , pp. 14-15
    • Abell, A.D.1    Taylor, J.M.2
  • 30
    • 0031251124 scopus 로고    scopus 로고
    • On the synthesis and the mechanism of formation of halogenated enol lactones
    • Kayser, M.M.; Zhu, J.; Hooper, D.L. On the synthesis and the mechanism of formation of halogenated enol lactones. Can. J. Chem. 1997, 75, 1322-1330.
    • (1997) Can. J. Chem. , vol.75 , pp. 1322-1330
    • Kayser, M.M.1    Zhu, J.2    Hooper, D.L.3
  • 31
    • 0001650014 scopus 로고    scopus 로고
    • Recent synthetic applications of the non-classical wittig reaction
    • Murphy, P.J.; Lee, S.E. Recent synthetic applications of the non-classical wittig reaction. J. Chem. Soc. Perkin Trans. 1 1999, 3049-3066.
    • (1999) J. Chem. Soc. Perkin Trans. 1 , pp. 3049-3066
    • Murphy, P.J.1    Lee, S.E.2
  • 32
    • 0000646938 scopus 로고
    • 3-chloroazirines. Photochemical formation and thermal isomerization
    • Ciabattoni, J.; Cabell, M., Jr. 3-Chloroazirines. Photochemical formation and thermal isomerization. J. Am. Chem. Soc. 1971, 93, 1482-1483.
    • (1971) J. Am. Chem. Soc. , vol.93 , pp. 1482-1483
    • Ciabattoni, J.1    Cabell, M.2
  • 34
    • 0026440798 scopus 로고
    • The conversion of carboxylic acids to keto phosphorane precursors of 1,2,3-vicinal tricarbonyl compounds
    • Wasserman, H.H.; Ennis, D.S.; Blum, C.A.; Rotello, V.M. The conversion of carboxylic acids to keto phosphorane precursors of 1,2,3-vicinal tricarbonyl compounds. Tetrahedron Lett. 1992, 33, 6003-6006.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 6003-6006
    • Wasserman, H.H.1    Ennis, D.S.2    Blum, C.A.3    Rotello, V.M.4
  • 35
    • 84954328981 scopus 로고    scopus 로고
    • SAINT and SADABS; Bruker AXS Inc.: Madison, WI, USA
    • Bruker, APEX2. In SAINT and SADABS; Bruker AXS Inc.: Madison, WI, USA, 2014.
    • (2014) APEX2
  • 36
    • 84937398809 scopus 로고    scopus 로고
    • SHELXT-integrated space-group and crystal-structure determination
    • Sheldrick, G. SHELXT-integrated space-group and crystal-structure determination. Acta Crystallogr. 2015, A71, 3-8.
    • (2015) Acta Crystallogr. , vol.A71 , pp. 3-8
    • Sheldrick, G.1
  • 37
    • 84937398809 scopus 로고    scopus 로고
    • Crystal structure refinement with SHELXL
    • Sheldrick, G. Crystal structure refinement with SHELXL. Acta Crystallogr. 2015, C71, 3-8.
    • (2015) Acta Crystallogr. , vol.C71 , pp. 3-8
    • Sheldrick, G.1
  • 38
    • 58849161857 scopus 로고    scopus 로고
    • Structure validation in chemical crystallography
    • Spek, A. Structure validation in chemical crystallography. Acta Crystallogr. 2009, D65, 148-155.
    • (2009) Acta Crystallogr. , vol.D65 , pp. 148-155
    • Spek, A.1


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