메뉴 건너뛰기




Volumn 38, Issue 6, 2005, Pages 460-468

Exploiting synthetic chemistry with mesoionic rings: Improvements achieved with thioisomünchnones

Author keywords

[No Author keywords available]

Indexed keywords


EID: 22244465857     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar040212r     Document Type: Article
Times cited : (37)

References (37)
  • 2
    • 0342548737 scopus 로고
    • Meso-Ionic Compounds
    • Katritzky, A. R., Boulton, A. J., Eds.; Academic Press: New York
    • Ollis, W. D.; Ramsden, C. A. Meso-Ionic Compounds. In Advances in Heterocyclic Chemistry, Katritzky, A. R., Boulton, A. J., Eds.; Academic Press: New York, 1976; Vol. 19, pp 1-122.
    • (1976) Advances in Heterocyclic Chemistry , vol.19 , pp. 1-122
    • Ollis, W.D.1    Ramsden, C.A.2
  • 3
    • 42049087420 scopus 로고
    • Mesoionic Heterocycles (1976-1980)
    • (b) Newton, C. G.; Ramsden, C. A. Mesoionic Heterocycles (1976-1980). Tetrahedron 1982, 38, 2965-3011.
    • (1982) Tetrahedron , vol.38 , pp. 2965-3011
    • Newton, C.G.1    Ramsden, C.A.2
  • 4
    • 1542534549 scopus 로고
    • A New Aromaticity Index and Its Application to Five-membered Ring Heterocycles
    • (c) Bird, C. W. A New Aromaticity Index and Its Application to Five-membered Ring Heterocycles. Tetrahedron 1985, 41, 1409-1414.
    • (1985) Tetrahedron , vol.41 , pp. 1409-1414
    • Bird, C.W.1
  • 7
    • 0001782197 scopus 로고
    • Mesoionic Ring Systems
    • Padwa, A., Ed.; Wiley: New York
    • Potts, K. T. Mesoionic Ring Systems. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Vol. 2, pp 1-82.
    • (1984) 1,3-Dipolar Cycloaddition Chemistry , vol.2 , pp. 1-82
    • Potts, K.T.1
  • 8
    • 0028301632 scopus 로고
    • Recent Advances in the Cycloaddition Chemistry of Isomünchnones and Thioisomünchnones, an Under-Utilized Class of Mesoionic Compounds
    • Osterhout, M. H.; Nadler, W. R.; Padwa, A. Recent Advances in the Cycloaddition Chemistry of Isomünchnones and Thioisomünchnones, an Under-Utilized Class of Mesoionic Compounds. Synthesis 1994, 123-141.
    • (1994) Synthesis , pp. 123-141
    • Osterhout, M.H.1    Nadler, W.R.2    Padwa, A.3
  • 11
    • 0000936734 scopus 로고
    • Ylide Formation from the Reaction of Carbenes and Carbenoids with Heteroatom Lone Pairs
    • (a) Padwa, A.; Hornbuckle, S. F. Ylide Formation from the Reaction of Carbenes and Carbenoids with Heteroatom Lone Pairs. Chem. Rev. 1991, 91, 263-309.
    • (1991) Chem. Rev. , vol.91 , pp. 263-309
    • Padwa, A.1    Hornbuckle, S.F.2
  • 12
    • 0026632575 scopus 로고
    • Application of Intramolecular Carbenoid Reactions in Organic Synthesis
    • (b) Padwa, A.; Krumpe, K. E. Application of Intramolecular Carbenoid Reactions in Organic Synthesis. Tetrahedron 1992, 48, 5385-5453.
    • (1992) Tetrahedron , vol.48 , pp. 5385-5453
    • Padwa, A.1    Krumpe, K.E.2
  • 13
    • 0037433246 scopus 로고    scopus 로고
    • The Development of a Catalytic Synthesis of Münchnones: A Simple Four-Component Coupling Approach to α-Amino Acid Derivatives
    • Dhawan, R.; Dghaym, R. D.; Arndtsen, B. A. The Development of a Catalytic Synthesis of Münchnones: A Simple Four-Component Coupling Approach to α-Amino Acid Derivatives. J. Am. Chem. Soc. 2003, 125, 1474-1475.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 1474-1475
    • Dhawan, R.1    Dghaym, R.D.2    Arndtsen, B.A.3
  • 14
    • 0001218092 scopus 로고    scopus 로고
    • Cycloaddition Chemistry of 1,3-Thiazolium-4-olate Systems. Reaction with Nitroalkenes and Interpretation of Results Using PM3 Calculations
    • and references therein
    • (a) Avalos, M.; Babiano, R.; Cabanillas, A.; Cintas, P.; Higes, F. J.; Jiménez, J. L.; Palacios, J. C. Cycloaddition Chemistry of 1,3-Thiazolium-4-olate Systems. Reaction with Nitroalkenes and Interpretation of Results Using PM3 Calculations. J. Org. Chem. 1996, 61, 3738-3748 and references therein.
    • (1996) J. Org. Chem. , vol.61 , pp. 3738-3748
    • Avalos, M.1    Babiano, R.2    Cabanillas, A.3    Cintas, P.4    Higes, F.J.5    Jiménez, J.L.6    Palacios, J.C.7
  • 16
    • 0000703412 scopus 로고
    • Mesoionic Compounds. 39. Synthesis of Some Functionally Substituted Five-Membered Systems Using 1,2-Bielectrophiles as Cyclization Agents
    • Potts, K. T.; Chen, S. J.; Kane, J.; Marshall, J. L. Mesoionic Compounds. 39. Synthesis of Some Functionally Substituted Five-Membered Systems Using 1,2-Bielectrophiles as Cyclization Agents. J. Org. Chem. 1977, 42, 1633-1638.
    • (1977) J. Org. Chem. , vol.42 , pp. 1633-1638
    • Potts, K.T.1    Chen, S.J.2    Kane, J.3    Marshall, J.L.4
  • 17
    • 0030761543 scopus 로고    scopus 로고
    • Structural Characterization of 4-Cyanoimidazolium-5-olate, 4,4-Diphenyl-5-imidazolinone, and 4,5-Dicyanoimidazole. A Novel Mesoionic Compound and Decoding of Intermolecular Hydrogen Bonds
    • and references therein
    • Barni, E.; Bianchi, R.; Gervasio, G.; Peters, A. T.; Viscardi, G. Structural Characterization of 4-Cyanoimidazolium-5-olate, 4,4-Diphenyl-5- imidazolinone, and 4,5-Dicyanoimidazole. A Novel Mesoionic Compound and Decoding of Intermolecular Hydrogen Bonds. J. Org. Chem. 1997, 62, 7037-7043 and references therein.
    • (1997) J. Org. Chem. , vol.62 , pp. 7037-7043
    • Barni, E.1    Bianchi, R.2    Gervasio, G.3    Peters, A.T.4    Viscardi, G.5
  • 18
    • 0030873356 scopus 로고    scopus 로고
    • Synthesis via a Carbohydrate-Derived Münchnone of Pyrrolopyridines (Indolizines) and Imidazopyridines, and Their Evaluation as Inhibitors of β-Glucosidases
    • Granier, T.; Gaiser, F.; Hintermann, L.; Vasella, A. Synthesis via a Carbohydrate-Derived Münchnone of Pyrrolopyridines (Indolizines) and Imidazopyridines, and Their Evaluation as Inhibitors of β-Glucosidases. Helv. Chim. Acta 1997, 80, 1443-1456.
    • (1997) Helv. Chim. Acta , vol.80 , pp. 1443-1456
    • Granier, T.1    Gaiser, F.2    Hintermann, L.3    Vasella, A.4
  • 23
    • 0035958485 scopus 로고    scopus 로고
    • Synergic Effect of Vicinal Stereocenters in [3+2] Cycloadditions of Carbohydrate Azadipolarophiles and Mesoionic Dipoles: Origin of Diastereofacial Selectivity
    • Avalos, M.; Babiano, R.; Cintas, P.; Clemente, F. R.; Gordillo, R.; Jiménez, J. L.; Palacios, J. C. Synergic Effect of Vicinal Stereocenters in [3+2] Cycloadditions of Carbohydrate Azadipolarophiles and Mesoionic Dipoles: Origin of Diastereofacial Selectivity. J. Org. Chem. 2001, 66, 5139-5145.
    • (2001) J. Org. Chem. , vol.66 , pp. 5139-5145
    • Avalos, M.1    Babiano, R.2    Cintas, P.3    Clemente, F.R.4    Gordillo, R.5    Jiménez, J.L.6    Palacios, J.C.7
  • 25
    • 0033592142 scopus 로고    scopus 로고
    • Unexpected Formation of β-Lactams and Penem Isosteres from Mesoionics: Sequential Ring-Opening-Rearrangement of [3+2] Cycloadducts
    • Avalos, M.; Babiano, R.; Cintas, P.; Hursthouse, M. B.; Jiménez, J. L.; Light, M. E.; López, I.; Palacios, J. C. Unexpected Formation of β-Lactams and Penem Isosteres from Mesoionics: Sequential Ring-Opening-Rearrangement of [3+2] Cycloadducts. Chem. Commun. 1999, 1589-1590.
    • (1999) Chem. Commun. , pp. 1589-1590
    • Avalos, M.1    Babiano, R.2    Cintas, P.3    Hursthouse, M.B.4    Jiménez, J.L.5    Light, M.E.6    López, I.7    Palacios, J.C.8
  • 27
    • 84981817890 scopus 로고
    • Possible Valence Tautomerism of a Mesoionic Oxazol-5-one with an Acylaminoketene
    • Huisgen, R.; Funke, E.; Schaefer, F. C.; Knorr, R. Possible Valence Tautomerism of a Mesoionic Oxazol-5-one with an Acylaminoketene. Angew. Chem., Int. Ed. Engl. 1967, 6, 367-368.
    • (1967) Angew. Chem., Int. Ed. Engl. , vol.6 , pp. 367-368
    • Huisgen, R.1    Funke, E.2    Schaefer, F.C.3    Knorr, R.4
  • 28
    • 0141485301 scopus 로고    scopus 로고
    • Fast Ring Opening of Unstable Mesoionic 1,3-Dioxolylium-4-olates to Acyloxyketenes. Formation of [2+2] Cycloadducts of Acyloxyketene with Several Ketenophiles
    • Hamaguchi, M.; Tomida, N.; Mochizuki, E.; Oshima, T. Fast Ring Opening of Unstable Mesoionic 1,3-Dioxolylium-4-olates to Acyloxyketenes. Formation of [2+2] Cycloadducts of Acyloxyketene with Several Ketenophiles. Tetrahedron Lett. 2003, 44, 7945-7948.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 7945-7948
    • Hamaguchi, M.1    Tomida, N.2    Mochizuki, E.3    Oshima, T.4
  • 30
    • 0042575724 scopus 로고    scopus 로고
    • 1,3-Dipolar Cycloaddition of 2-Dialkylaminothioisomünchnones with Aliphatic Aldehydes: Synthesis of β-Lactams and Thiiranes, Structure Elucidation, and Rationale for Chemoselective Fragmentation of Cycloadducts
    • Avalos, M.; Babiano, R.; Cintas, P.; Clemente, F. R.; Gordillo, R.; Jiménez, J. L.; Palacios, J. C. 1,3-Dipolar Cycloaddition of 2-Dialkylaminothioisomünchnones with Aliphatic Aldehydes: Synthesis of β-Lactams and Thiiranes, Structure Elucidation, and Rationale for Chemoselective Fragmentation of Cycloadducts. J. Org. Chem. 2003, 68, 6338-6348.
    • (2003) J. Org. Chem. , vol.68 , pp. 6338-6348
    • Avalos, M.1    Babiano, R.2    Cintas, P.3    Clemente, F.R.4    Gordillo, R.5    Jiménez, J.L.6    Palacios, J.C.7
  • 31
    • 0001163616 scopus 로고
    • Reaction of N-Substituted Thioamides with gem-Dicyano Epoxides: A New Synthetic Route to Anhydro-4-hydroxythiazolium Hydroxides
    • Baudy, M.; Robert, A.; Foucaud, A. Reaction of N-Substituted Thioamides with gem-Dicyano Epoxides: A New Synthetic Route to Anhydro-4-hydroxythiazolium Hydroxides. J. Org. Chem. 1978, 43, 3732-3736.
    • (1978) J. Org. Chem. , vol.43 , pp. 3732-3736
    • Baudy, M.1    Robert, A.2    Foucaud, A.3
  • 33
    • 0032495790 scopus 로고    scopus 로고
    • Intramolecular Nonbonded S⋯O Interaction Recognized in (Acylimino)thiadiazoline Derivatives as Angiotensin II Receptor Antagonists and Related Compounds
    • Nagao, Y.; Hirata, T.; Goto, S.; Sano, S.; Kakehi, A.; Iizuka, K.; Shiro, M. Intramolecular Nonbonded S⋯O Interaction Recognized in (Acylimino)thiadiazoline Derivatives as Angiotensin II Receptor Antagonists and Related Compounds. J. Am. Chem. Soc. 1998, 120, 3104-3110.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 3104-3110
    • Nagao, Y.1    Hirata, T.2    Goto, S.3    Sano, S.4    Kakehi, A.5    Iizuka, K.6    Shiro, M.7
  • 35
    • 0030564746 scopus 로고    scopus 로고
    • Mesoionic Rings as Efficient Asymmetric Bridges for the Design of Compounds with Large Optical Nonlinearities
    • (a) Moura, G. L. C.; Simas, A. M.; Miller, J. Mesoionic Rings as Efficient Asymmetric Bridges for the Design of Compounds with Large Optical Nonlinearities. Chem. Phys. Lett. 1996, 257, 639-646.
    • (1996) Chem. Phys. Lett. , vol.257 , pp. 639-646
    • Moura, G.L.C.1    Simas, A.M.2    Miller, J.3
  • 37
    • 0141869055 scopus 로고    scopus 로고
    • An Unexpectedly Simple NIR Dye for 1.1 μ with a Central Mesoionic Structure
    • For a perspective: Langhals, H. An Unexpectedly Simple NIR Dye for 1.1 μ with a Central Mesoionic Structure. Angew. Chem., Int. Ed. 2003, 42, 4286-4288.
    • (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 4286-4288
    • Langhals, H.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.