메뉴 건너뛰기




Volumn 52, Issue 8, 1996, Pages 2827-2838

A facile and regio-and stereo-selective preparation of bicyclic guanidines by iodocyclization of 3-(alk-2-enyl)-2-(substituted amino)-1-imidazolin-4-ones 1

Author keywords

[No Author keywords available]

Indexed keywords

GUANIDINE DERIVATIVE; IMIDAZO[1,2 A]IMIDAZOLE DERIVATIVE; IMIDAZO[1,2 A]PYRIMIDINE DERIVATIVE; IMIDAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0030027989     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00004-X     Document Type: Article
Times cited : (39)

References (34)
  • 2
    • 0018242844 scopus 로고
    • Ishikawa, F.; Kosasayama, A.; Nakamura, S,; Konno, T. Chem. Pharm. Bull. 1978, 26, 3658; Ishikawa, F.; Kosasayama, A.; Konno, T. Ibid. 1978, 26, 3666; Kosasayama, A.; Watanabe, Y.; Higashi, K.; Ishikawa, F. Ibid. 1979, 27, 831; Kosasayama, A.; Konno, T.; Higashi, K.; Ishikawa, F. Ibid. 1979, 27, 841.
    • (1978) Chem. Pharm. Bull. , vol.26 , pp. 3658
    • Ishikawa, F.1    Kosasayama, A.2    Nakamura, S.3    Konno, T.4
  • 3
    • 0018258338 scopus 로고
    • Ishikawa, F.; Kosasayama, A.; Nakamura, S,; Konno, T. Chem. Pharm. Bull. 1978, 26, 3658; Ishikawa, F.; Kosasayama, A.; Konno, T. Ibid. 1978, 26, 3666; Kosasayama, A.; Watanabe, Y.; Higashi, K.; Ishikawa, F. Ibid. 1979, 27, 831; Kosasayama, A.; Konno, T.; Higashi, K.; Ishikawa, F. Ibid. 1979, 27, 841.
    • (1978) Chem. Pharm. Bull. , vol.26 , pp. 3666
    • Ishikawa, F.1    Kosasayama, A.2    Konno, T.3
  • 4
    • 0018388479 scopus 로고
    • Ishikawa, F.; Kosasayama, A.; Nakamura, S,; Konno, T. Chem. Pharm. Bull. 1978, 26, 3658; Ishikawa, F.; Kosasayama, A.; Konno, T. Ibid. 1978, 26, 3666; Kosasayama, A.; Watanabe, Y.; Higashi, K.; Ishikawa, F. Ibid. 1979, 27, 831; Kosasayama, A.; Konno, T.; Higashi, K.; Ishikawa, F. Ibid. 1979, 27, 841.
    • (1979) Chem. Pharm. Bull. , vol.27 , pp. 831
    • Kosasayama, A.1    Watanabe, Y.2    Higashi, K.3    Ishikawa, F.4
  • 5
    • 0018361272 scopus 로고
    • Ishikawa, F.; Kosasayama, A.; Nakamura, S,; Konno, T. Chem. Pharm. Bull. 1978, 26, 3658; Ishikawa, F.; Kosasayama, A.; Konno, T. Ibid. 1978, 26, 3666; Kosasayama, A.; Watanabe, Y.; Higashi, K.; Ishikawa, F. Ibid. 1979, 27, 831; Kosasayama, A.; Konno, T.; Higashi, K.; Ishikawa, F. Ibid. 1979, 27, 841.
    • (1979) Chem. Pharm. Bull. , vol.27 , pp. 841
    • Kosasayama, A.1    Konno, T.2    Higashi, K.3    Ishikawa, F.4
  • 8
    • 0028657560 scopus 로고
    • For recent reviews on the synthetic utilities of carbodiimides: Molina, P.; Vilaplana, M. J. Synthesis 1994, 1197; Eguchi, S.; Matsushita, Y.; Yamashita, K. Org. Prep. Proced. Int. 1992, 24, 209; Gololobov, Y. G.; Kasukhin, L. F. Tetrahedron 1992, 48, 1353; Barluenga, J.; Palacios, F. Org, Prep. Procd. Int. 1992, 23, 1.
    • (1994) Synthesis , pp. 1197
    • Molina, P.1    Vilaplana, M.J.2
  • 9
    • 84952142578 scopus 로고
    • For recent reviews on the synthetic utilities of carbodiimides: Molina, P.; Vilaplana, M. J. Synthesis 1994, 1197; Eguchi, S.; Matsushita, Y.; Yamashita, K. Org. Prep. Proced. Int. 1992, 24, 209; Gololobov, Y. G.; Kasukhin, L. F. Tetrahedron 1992, 48, 1353; Barluenga, J.; Palacios, F. Org, Prep. Procd. Int. 1992, 23, 1.
    • (1992) Org. Prep. Proced. Int. , vol.24 , pp. 209
    • Eguchi, S.1    Matsushita, Y.2    Yamashita, K.3
  • 10
    • 0026516860 scopus 로고
    • For recent reviews on the synthetic utilities of carbodiimides: Molina, P.; Vilaplana, M. J. Synthesis 1994, 1197; Eguchi, S.; Matsushita, Y.; Yamashita, K. Org. Prep. Proced. Int. 1992, 24, 209; Gololobov, Y. G.; Kasukhin, L. F. Tetrahedron 1992, 48, 1353; Barluenga, J.; Palacios, F. Org, Prep. Procd. Int. 1992, 23, 1.
    • (1992) Tetrahedron , vol.48 , pp. 1353
    • Gololobov, Y.G.1    Kasukhin, L.F.2
  • 11
    • 84912958679 scopus 로고
    • For recent reviews on the synthetic utilities of carbodiimides: Molina, P.; Vilaplana, M. J. Synthesis 1994, 1197; Eguchi, S.; Matsushita, Y.; Yamashita, K. Org. Prep. Proced. Int. 1992, 24, 209; Gololobov, Y. G.; Kasukhin, L. F. Tetrahedron 1992, 48, 1353; Barluenga, J.; Palacios, F. Org, Prep. Procd. Int. 1992, 23, 1.
    • (1992) Org, Prep. Procd. Int. , vol.23 , pp. 1
    • Barluenga, J.1    Palacios, F.2
  • 12
    • 15844366864 scopus 로고
    • For recent reviews on the iodocyclizations: Boivin, T. L. B. Tetrahedron 1987, 43, 3309; Cardillo, G.; Orena, M. Ibid. 1990, 46, 3321.
    • (1987) Tetrahedron , vol.43 , pp. 3309
    • Boivin, T.L.B.1
  • 13
    • 0001657273 scopus 로고
    • For recent reviews on the iodocyclizations: Boivin, T. L. B. Tetrahedron 1987, 43, 3309; Cardillo, G.; Orena, M. Ibid. 1990, 46, 3321.
    • (1990) Tetrahedron , vol.46 , pp. 3321
    • Cardillo, G.1    Orena, M.2
  • 14
    • 0344361923 scopus 로고
    • Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734; Baldwin, J. E.; Cutting, J.; Dupont, W. Kruse, L.; Silberman, L.; Thomas, R. C. Ibid. 1976, 736; Baldwin, J. E. Ibid. 1976, 738.
    • (1976) J. Chem. Soc., Chem. Commun. , pp. 734
    • Baldwin, J.E.1
  • 16
    • 37049113016 scopus 로고
    • Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734; Baldwin, J. E.; Cutting, J.; Dupont, W. Kruse, L.; Silberman, L.; Thomas, R. C. Ibid. 1976, 736; Baldwin, J. E. Ibid. 1976, 738.
    • (1976) J. Chem. Soc., Chem. Commun. , pp. 738
    • Baldwin, J.E.1
  • 17
    • 0010788690 scopus 로고
    • Litchman, W. M.; Grant, D. M. J. Am. Chem. Soc. 1968, 90, 1400; Howarth, O. W.; Lynch, R. J. Mol. Phys. 1968, 15, 431; Miyajima, G.; Takahashi, K. J. Phys. Chem. 1971, 75, 331 and 3766.
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 1400
    • Litchman, W.M.1    Grant, D.M.2
  • 18
    • 84945611272 scopus 로고
    • Litchman, W. M.; Grant, D. M. J. Am. Chem. Soc. 1968, 90, 1400; Howarth, O. W.; Lynch, R. J. Mol. Phys. 1968, 15, 431; Miyajima, G.; Takahashi, K. J. Phys. Chem. 1971, 75, 331 and 3766.
    • (1968) Mol. Phys. , vol.15 , pp. 431
    • Howarth, O.W.1    Lynch, R.J.2
  • 19
    • 0038842558 scopus 로고
    • Litchman, W. M.; Grant, D. M. J. Am. Chem. Soc. 1968, 90, 1400; Howarth, O. W.; Lynch, R. J. Mol. Phys. 1968, 15, 431; Miyajima, G.; Takahashi, K. J. Phys. Chem. 1971, 75, 331 and 3766.
    • (1971) J. Phys. Chem. , vol.75 , pp. 331
    • Miyajima, G.1    Takahashi, K.2
  • 20
    • 85029981818 scopus 로고    scopus 로고
    • note
    • The authors have deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained on request from The Director, Cambridge Crystallographic Data Centre, University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, U.K.
  • 21
    • 84987089586 scopus 로고
    • Jin, S. Q.; Liu, R. Z. Int. J. Quant. Chem. 1984, 25, 699; Chamberlin, A. R.; Mulholland, Jr., R. L.; Kahn, S. D.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 672. Also see the references cited therein.
    • (1984) Int. J. Quant. Chem. , vol.25 , pp. 699
    • Jin, S.Q.1    Liu, R.Z.2
  • 23
    • 0009497237 scopus 로고
    • For recent papers: a) Poirier, R. A.; Mezey, P. G.; Yates, K.; Csizmadia, I. G. J. Mol. Struct. 1981, 85, 153; Jin, S. Q.; Liu, R. Z. Int. J. Quant. Chem. 1984, 25, 699; Galland, B.; Evleth, E. M.; Ruasse, M. -F. J. Chem. Soc., Chem. Commun. 1990, 898;
    • (1981) J. Mol. Struct. , vol.85 , pp. 153
    • Poirier, R.A.1    Mezey, P.G.2    Yates, K.3    Csizmadia, I.G.4
  • 24
    • 84987089586 scopus 로고
    • For recent papers: a) Poirier, R. A.; Mezey, P. G.; Yates, K.; Csizmadia, I. G. J. Mol. Struct. 1981, 85, 153; Jin, S. Q.; Liu, R. Z. Int. J. Quant. Chem. 1984, 25, 699; Galland, B.; Evleth, E. M.; Ruasse, M. -F. J. Chem. Soc., Chem. Commun. 1990, 898;
    • (1984) Int. J. Quant. Chem. , vol.25 , pp. 699
    • Jin, S.Q.1    Liu, R.Z.2
  • 25
    • 37049081172 scopus 로고
    • For recent papers: a) Poirier, R. A.; Mezey, P. G.; Yates, K.; Csizmadia, I. G. J. Mol. Struct. 1981, 85, 153; Jin, S. Q.; Liu, R. Z. Int. J. Quant. Chem. 1984, 25, 699; Galland, B.; Evleth, E. M.; Ruasse, M. -F. J. Chem. Soc., Chem. Commun. 1990, 898;
    • (1990) J. Chem. Soc., Chem. Commun. , pp. 898
    • Galland, B.1    Evleth, E.M.2    Ruasse, M.-F.3
  • 27
    • 0001411148 scopus 로고
    • c) Hamilton, T. P.; Schaefer, III, H. F. J. Am. Chem. Soc. 1990, 112, 8260; Sperka, J.; Liotta, D. C. Heterocycles 1993, 35, 701. Also see the references cited therein.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 8260
    • Hamilton, T.P.1    Schaefer H.F. III2
  • 28
    • 0040620429 scopus 로고
    • Also see the references cited therein
    • c) Hamilton, T. P.; Schaefer, III, H. F. J. Am. Chem. Soc. 1990, 112, 8260; Sperka, J.; Liotta, D. C. Heterocycles 1993, 35, 701. Also see the references cited therein.
    • (1993) Heterocycles , vol.35 , pp. 701
    • Sperka, J.1    Liotta, D.C.2
  • 30
    • 85029977736 scopus 로고    scopus 로고
    • "MOPAC program version 6, QCPE No. 455," 1990, Department of Chemistry, Indiana University, Bloomington, IN 47405
    • "MOPAC program version 6, QCPE No. 455," 1990, Department of Chemistry, Indiana University, Bloomington, IN 47405.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.