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Volumn 65, Issue 18, 2000, Pages 5768-5773

Designing large triangular chiral macrocycles: Efficient [3 + 3] diamine-dialdehyde condensations based on conformational bias

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; DIAMINE DERIVATIVE; MACROCYCLIC COMPOUND;

EID: 0041304121     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000623v     Document Type: Article
Times cited : (166)

References (37)
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    • [2 + 2] condensation of aromatic dialdehydes with aliphatic diamines has been reported to give large-membered macrocyclic Schiff bases: (a) Jazwinski, J.; Lehn, J.-M.; Méric, R.; Vigneron, J.-P.; Cesario, M.; Guilham, J.; Pascard, C. Tetrahedron Lett. 1987, 28, 3489-3492. (b) Menif, R.; Martell, A. E. J. Chem. Soc., Chem. Commun. 1989, 1521-1523. (c) Chen, D.; Martell, A. E. Tetrahedron 1991, 47, 6895-6902. (d) Comba, P.; Fath, A.; Hambley, T. W.; Richens, D. T. Angew. Chem., Int. Ed. Engl. 1995, 34, 1883-1885. (e) Comba, P.; Hambley, T. W.; Hifenhaus, P.; Richens, D. T. J. Chem. Soc., Dalton Trans. 1996, 533-539.
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    • [2 + 2] condensation of aromatic dialdehydes with aliphatic diamines has been reported to give large-membered macrocyclic Schiff bases: (a) Jazwinski, J.; Lehn, J.-M.; Méric, R.; Vigneron, J.-P.; Cesario, M.; Guilham, J.; Pascard, C. Tetrahedron Lett. 1987, 28, 3489-3492. (b) Menif, R.; Martell, A. E. J. Chem. Soc., Chem. Commun. 1989, 1521-1523. (c) Chen, D.; Martell, A. E. Tetrahedron 1991, 47, 6895-6902. (d) Comba, P.; Fath, A.; Hambley, T. W.; Richens, D. T. Angew. Chem., Int. Ed. Engl. 1995, 34, 1883-1885. (e) Comba, P.; Hambley, T. W.; Hifenhaus, P.; Richens, D. T. J. Chem. Soc., Dalton Trans. 1996, 533-539.
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    • 0025873601 scopus 로고
    • [2 + 2] condensation of aromatic dialdehydes with aliphatic diamines has been reported to give large-membered macrocyclic Schiff bases: (a) Jazwinski, J.; Lehn, J.-M.; Méric, R.; Vigneron, J.-P.; Cesario, M.; Guilham, J.; Pascard, C. Tetrahedron Lett. 1987, 28, 3489-3492. (b) Menif, R.; Martell, A. E. J. Chem. Soc., Chem. Commun. 1989, 1521-1523. (c) Chen, D.; Martell, A. E. Tetrahedron 1991, 47, 6895-6902. (d) Comba, P.; Fath, A.; Hambley, T. W.; Richens, D. T. Angew. Chem., Int. Ed. Engl. 1995, 34, 1883-1885. (e) Comba, P.; Hambley, T. W.; Hifenhaus, P.; Richens, D. T. J. Chem. Soc., Dalton Trans. 1996, 533-539.
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  • 6
    • 33748832062 scopus 로고
    • [2 + 2] condensation of aromatic dialdehydes with aliphatic diamines has been reported to give large-membered macrocyclic Schiff bases: (a) Jazwinski, J.; Lehn, J.-M.; Méric, R.; Vigneron, J.-P.; Cesario, M.; Guilham, J.; Pascard, C. Tetrahedron Lett. 1987, 28, 3489-3492. (b) Menif, R.; Martell, A. E. J. Chem. Soc., Chem. Commun. 1989, 1521-1523. (c) Chen, D.; Martell, A. E. Tetrahedron 1991, 47, 6895-6902. (d) Comba, P.; Fath, A.; Hambley, T. W.; Richens, D. T. Angew. Chem., Int. Ed. Engl. 1995, 34, 1883-1885. (e) Comba, P.; Hambley, T. W.; Hifenhaus, P.; Richens, D. T. J. Chem. Soc., Dalton Trans. 1996, 533-539.
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    • 33748511441 scopus 로고    scopus 로고
    • [2 + 2] condensation of aromatic dialdehydes with aliphatic diamines has been reported to give large-membered macrocyclic Schiff bases: (a) Jazwinski, J.; Lehn, J.-M.; Méric, R.; Vigneron, J.-P.; Cesario, M.; Guilham, J.; Pascard, C. Tetrahedron Lett. 1987, 28, 3489-3492. (b) Menif, R.; Martell, A. E. J. Chem. Soc., Chem. Commun. 1989, 1521-1523. (c) Chen, D.; Martell, A. E. Tetrahedron 1991, 47, 6895-6902. (d) Comba, P.; Fath, A.; Hambley, T. W.; Richens, D. T. Angew. Chem., Int. Ed. Engl. 1995, 34, 1883-1885. (e) Comba, P.; Hambley, T. W.; Hifenhaus, P.; Richens, D. T. J. Chem. Soc., Dalton Trans. 1996, 533-539.
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    • For applications of polyazamacrocycles see: (a) Smidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609-1646. (b) Bencini, A.; Bianchi, A.; Paoletti, P.; Paoli, P. Coord. Chem. Rev. 1992, 120, 51- 85. (c) Dietrich, B.; Hosseini, M. W.; Lehn, J.-M.; Sessions, R. B. Helv. Chim. Acta 1983, 66, 1262-1278.
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    • For applications of polyazamacrocycles see: (a) Smidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609-1646. (b) Bencini, A.; Bianchi, A.; Paoletti, P.; Paoli, P. Coord. Chem. Rev. 1992, 120, 51-85. (c) Dietrich, B.; Hosseini, M. W.; Lehn, J.-M.; Sessions, R. B. Helv. Chim. Acta 1983, 66, 1262-1278.
    • (1992) Coord. Chem. Rev. , vol.120 , pp. 51-85
    • Bencini, A.1    Bianchi, A.2    Paoletti, P.3    Paoli, P.4
  • 32
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    • For applications of polyazamacrocycles see: (a) Smidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609-1646. (b) Bencini, A.; Bianchi, A.; Paoletti, P.; Paoli, P. Coord. Chem. Rev. 1992, 120, 51- 85. (c) Dietrich, B.; Hosseini, M. W.; Lehn, J.-M.; Sessions, R. B. Helv. Chim. Acta 1983, 66, 1262-1278.
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  • 33
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    • Very recently, MMX calculations on appropriate model molecules were used to predict the course of intramolecular ring closures to give thiamacrocycles: Abramovitch, R. A.; Ye, X.; Pennington, W. T.; Schimek, G.; Bogdal, D. J. Org. Chem. 2000, 65, 343-351.
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    • Abramovitch, R.A.1    Ye, X.2    Pennington, W.T.3    Schimek, G.4    Bogdal, D.5
  • 34
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    • For comparison, from the two reported X-ray crystal analyses of bis-salicylidene derivatives of trans-1,2-diaminocyclohexane we calculated the ω (H-C-N=C) angles respectively as 4.7°, -8.8°, and 5.8°, -3.7°. See: (a) Cannadine, J. C.; Corden, J. P.; Errington, W.; Moore, P.; Wallbridge, M. G. H. Acta Crystallogr. 1996, C52, 1014-1017. (b) Liu, Q.; Ding, M.; Lin, Y.; Xing, Y. Acta Crystallogr. 1997, C53, 1971-1673.
    • (1996) Acta Crystallogr. , vol.C52 , pp. 1014-1017
    • Cannadine, J.C.1    Corden, J.P.2    Errington, W.3    Moore, P.4    Wallbridge, M.G.H.5
  • 35
    • 0037493537 scopus 로고    scopus 로고
    • For comparison, from the two reported X-ray crystal analyses of bis-salicylidene derivatives of trans-1,2-diaminocyclohexane we calculated the ω (H-C-N=C) angles respectively as 4.7°, -8.8°, and 5.8°, -3.7°. See: (a) Cannadine, J. C.; Corden, J. P.; Errington, W.; Moore, P.; Wallbridge, M. G. H. Acta Crystallogr. 1996, C52, 1014- 1017. (b) Liu, Q.; Ding, M.; Lin, Y.; Xing, Y. Acta Crystallogr. 1997, C53, 1971-1673.
    • (1997) Acta Crystallogr. , vol.C53 , pp. 1971-11673
    • Liu, Q.1    Ding, M.2    Lin, Y.3    Xing, Y.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.