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Volumn 63, Issue 19, 2007, Pages 4039-4047

Synthesis of tetrahydroisoquinolines and isochromans via Pictet-Spengler reactions catalyzed by Brønsted acid-surfactant-combined catalyst in aqueous media

Author keywords

Br nsted acid; Isochroman; Isoquinoline; Pictet Spengler reaction; Surfactant

Indexed keywords

1 CYCLOHEXYL 6,7 DIMETHOXY 3,4 DIHYDRO 1H ISOCHROMENE; 1 HEXYL 6 METHOXY 3,4 DIHYDRO 1H ISOCHROMENE; 6 METHOXY 1 PHENYL 3,4 DIHYDRO 1H ISOCHROMENE; 6,7 DIMETHOXY 1 ETHYL 3,4 DIHYDRO 1H ISOCHROMENE; 6,7 DIMETHOXY 1 ISOPROPYL 3,4 DIHYDRO 1H ISOCHROMENE; 6,7 DIMETHOXY 1 PHENYL 3,4 DIHYDRO 1H ISOCHROMENE; 6,7 DIMETHOXY 1 UNDECYL 3,4 DIHYDRO 1H ISOCHROMENE; 6,7 DIMETHOXY 3,4 DIHYDRO 1H ISOCHROMENE; BRONSTED ACID; DIMETHOXY 1 HEXYL 3,4 DIHYDRO 1H ISOCHROMENE; ISOCHROMAN DERIVATIVE; N (METHOXYCARBONYL) 1 HEXYL 6 HYDROXY 1,2,3,4 TETRAHYDROISOQUINOLINE; N (METHOXYCARBONYL) 1 HEXYL 6 METHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE; N (METHOXYCARBONYL) 1 HEXYL 8 HYDROXY 1,2,3,4 TETRAHYDROISOQUINOLINE; N (METHOXYCARBONYL) 1 HEXYL 8 METHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE; N (METHOXYCARBONYL) 1 ISOPROPYL 6,7 DIMETHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE; N (METHOXYCARBONYL) 1 PHENYL 6 HYDROXY 1,2,3,4 TETRAHYDROISOQUINOLINE; N (METHOXYCARBONYL) 1 PHENYL 6 METHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE; N (METHOXYCARBONYL) 1 PHENYL 8 HYDROXY 1,2,3,4 TETRAHYDROISOQUINOLINE; N (METHOXYCARBONYL) 1 PHENYL 8 METHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE; N (METHOXYCARBONYL) 6,7 DIMETHYLOXY 1 ETHYL 1,2,3,4 TETRAHYDROISOQUINOLINE; N (METHOXYCARBONYL) 6,7 DIMETHYLOXY 1 HEXYL 1,2,3,4 TETRAHYDROISOQUINOLINE; N (METHOXYCARBONYL) 6,7 DIMETHYLOXY 1 PHENYL 1,2,3,4 TETRAHYDROISOQUINOLINE; N (METHOXYCARBONYL) 6,7 DIMETHYLOXY 1 UNDECYL 1,2,3,4 TETRAHYDROISOQUINOLINE; N (METHOXYCARBONYL) 6,7 DIMETHYLOXY 1,2,3,4 TETRAHYDROXYISOQUINOLINE; SURFACTANT; TETRAHYDROISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 34047123624     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.02.123     Document Type: Article
Times cited : (42)

References (54)
  • 2
    • 34047139724 scopus 로고    scopus 로고
    • For reviews:
  • 5
    • 34047128451 scopus 로고    scopus 로고
    • For reviews, see:
  • 6
    • 24744434242 scopus 로고
    • Saxton J.E. (Ed), Wiley-Interscience, New York, NY Part 4 (The Monoterpenoid Indole Alkaloids)
    • Brown R.T. In: Saxton J.E. (Ed). Indoles (1983), Wiley-Interscience, New York, NY Part 4 (The Monoterpenoid Indole Alkaloids)
    • (1983) Indoles
    • Brown, R.T.1
  • 7
    • 3042742899 scopus 로고    scopus 로고
    • and references therein
    • Bentley K.W. Nat. Prod. Rep. 21 (2004) 395 and references therein
    • (2004) Nat. Prod. Rep. , vol.21 , pp. 395
    • Bentley, K.W.1
  • 16
    • 31544445537 scopus 로고    scopus 로고
    • For reviews, see: and references therein
    • For reviews, see:. Larghi E.L., and Kaufman T.S. Synthesis (2006) 187 and references therein
    • (2006) Synthesis , pp. 187
    • Larghi, E.L.1    Kaufman, T.S.2
  • 21
    • 34047159037 scopus 로고    scopus 로고
    • Although the use of aqueous EtOH as solvent has been reported, they require a large excess of strong Brønsted acid. See:
  • 23
    • 0004252595 scopus 로고    scopus 로고
    • Grieco P.A. (Ed), Blackie Academic and Professional, London
    • In: Grieco P.A. (Ed). Organic Synthesis in Water (1998), Blackie Academic and Professional, London
    • (1998) Organic Synthesis in Water
  • 37
    • 34047144223 scopus 로고    scopus 로고
    • note
    • About the Pictet-Spengler reactions of β-arylethyl amine in water, it has been reported that hydrochloride salt of 3,4-dimethoxyphenethylamine (1) gave no cyclized product. In our preliminary research, hydrochloride salt of 3,4-dimethoxyphenethylamine with n-heptanal did not brought about cyclization in water as well. See Ref. 8a.
  • 40
    • 34047137525 scopus 로고    scopus 로고
    • note
    • Critical micelle concentration: 6.9 mM (by electric conductivity analysis).
  • 41
    • 34047099608 scopus 로고    scopus 로고
    • For perfluoroalkylsulfonic acid-catalyzed reactions in aqueous media, see: Nishikido, J. JP Patent 2001-328954; 2001.
  • 42
    • 34047101191 scopus 로고    scopus 로고
    • note
    • In presence of 20 mol % PFOSA, 3,4-dimethoxyphenethylamine with n-heptanal in water gave no cyclized product at rt for 24 h.
  • 44
    • 0001435731 scopus 로고
    • It has been reported that fluorinated alcohols are more strongly partitioned in the micelles with both the hydrocarbon and fluorocarbon surfactants than hydrocarbon alcohols. See: See also Ref. 24
    • It has been reported that fluorinated alcohols are more strongly partitioned in the micelles with both the hydrocarbon and fluorocarbon surfactants than hydrocarbon alcohols. See:. Muto J., Yoda K., Yoshida N., Esumi K., Meguro K., Binana-Limbele W., and Zana R. J. Colloid Interface Sci. 130 (1989) 165 See also Ref. 24
    • (1989) J. Colloid Interface Sci. , vol.130 , pp. 165
    • Muto, J.1    Yoda, K.2    Yoshida, N.3    Esumi, K.4    Meguro, K.5    Binana-Limbele, W.6    Zana, R.7
  • 45
    • 34047108959 scopus 로고    scopus 로고
    • note
    • We have carried out the pH determination of catalyst (80 μmol) solutions in HFIP (130 μL)-water (1 mL) by pH meter. PFOSA: 1.15. DBSA: 1.21. TfOH: 1.15.
  • 46
    • 34047190670 scopus 로고    scopus 로고
    • Clustering of HFIP in water has been reported in:
  • 49
    • 0346970844 scopus 로고    scopus 로고
    • For review about fluorinated alcohols as reaction solvents, see:
    • For review about fluorinated alcohols as reaction solvents, see:. Begue J.P., Bonnet-delpon D., and Crousse B. Synlett (2004) 18
    • (2004) Synlett , pp. 18
    • Begue, J.P.1    Bonnet-delpon, D.2    Crousse, B.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.