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;
ADDITION REACTION;
AQUEOUS SOLUTION;
ARTICLE;
CATALYSIS;
CATALYST;
PICTET SPENGLER REACTION;
PRIORITY JOURNAL;
2
34047139724
For reviews:
3
0003417469
Trost B.M. (Ed), Pergamon, Oxford Chapter 4.2
Bringmann G., Ewers C.L.J., and Walter R. In: Trost B.M. (Ed). Comprehensive Organic Synthesis Vol. 6 (1991), Pergamon, Oxford 733 Chapter 4.2
(1991)
Comprehensive Organic Synthesis
, vol.6
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Bringmann, G.1
Ewers, C.L.J.2
Walter, R.3
5
34047128451
For reviews, see:
6
24744434242
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
and references therein
Bentley K.W. Nat. Prod. Rep. 21 (2004) 395 and references therein
(2004)
Nat. Prod. Rep.
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Bentley, K.W.1
13
84893855512
Freter K., Huebner H., Metz H., Schroeder H.D., and Zeile K. Justus Liebigs Ann. Chem. 684 (1965) 159
(1965)
Justus Liebigs Ann. Chem.
, vol.684
, pp. 159
Freter, K.1
Huebner, H.2
Metz, H.3
Schroeder, H.D.4
Zeile, K.5
14
0030970535
Kawai M., Deng Y., Kimura I., Yamamura H., Araki S., and Naoi M. Tetrahedron: Asymmetry 9 (1997) 1487
(1997)
Tetrahedron: Asymmetry
, vol.9
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Kawai, M.1
Deng, Y.2
Kimura, I.3
Yamamura, H.4
Araki, S.5
Naoi, M.6
16
31544445537
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
Although the use of aqueous EtOH as solvent has been reported, they require a large excess of strong Brønsted acid. See:
22
84980314164
Kametani T., Kigasawa K., Hiiragi M., Ishimaru H., Wagatsuma N., Haga S., and Kusama O. J. Heterocycl. Chem. 12 (1975) 851
(1975)
J. Heterocycl. Chem.
, vol.12
, pp. 851
Kametani, T.1
Kigasawa, K.2
Hiiragi, M.3
Ishimaru, H.4
Wagatsuma, N.5
Haga, S.6
Kusama, O.7
23
0004252595
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
32
4444383998
Jin T.S., Zhang J.S., Xiao J.C., Wang A.Q., and Li T.S. Synlett (2004) 866
(2004)
Synlett
, pp. 866
Jin, T.S.1
Zhang, J.S.2
Xiao, J.C.3
Wang, A.Q.4
Li, T.S.5
35
1842430777
For review, see:
For review, see:. Maryanoff B.E., Zhang C.-H., Cohen J.H., Turchi I.J., and Maryanoff C.A. Chem. Rev. 104 (2004) 1431
(2004)
Chem. Rev.
, vol.104
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Maryanoff, B.E.1
Zhang, C.-H.2
Cohen, J.H.3
Turchi, I.J.4
Maryanoff, C.A.5
36
25444520789
For recent example, see:
For recent example, see:. Danetz J.R., Ciccolini R.P., Froling M., Paap S.M., Allen A.J., Holmes A.B., Tester J.W., and Danheiser R.L. Chem. Commun. (2005) 4465
(2005)
Chem. Commun.
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Danetz, J.R.1
Ciccolini, R.P.2
Froling, M.3
Paap, S.M.4
Allen, A.J.5
Holmes, A.B.6
Tester, J.W.7
Danheiser, R.L.8
37
34047144223
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
note
Critical micelle concentration: 6.9 mM (by electric conductivity analysis).
41
34047099608
For perfluoroalkylsulfonic acid-catalyzed reactions in aqueous media, see: Nishikido, J. JP Patent 2001-328954; 2001.
42
34047101191
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
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
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
Clustering of HFIP in water has been reported in:
48
0142026572
Yoshida K., Yamaguchi T., Adachi T., Otomo T., Matsuo D., Takamuku T., and Nishi N. J. Chem. Phys. 119 (2003) 6132
(2003)
J. Chem. Phys.
, vol.119
, pp. 6132
Yoshida, K.1
Yamaguchi, T.2
Adachi, T.3
Otomo, T.4
Matsuo, D.5
Takamuku, T.6
Nishi, N.7
49
0346970844
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
50
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Kaim L.E., Grimaud L., Lee A., Perroux Y., and Tirla C. Org. Lett. 6 (2004) 381
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Org. Lett.
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Kaim, L.E.1
Grimaud, L.2
Lee, A.3
Perroux, Y.4
Tirla, C.5
51
0037156592
Salvatore R.N., Chu F., Nagle A.S., Kapxhiu E.A., Cross R.M., and Jung K.W. Tetrahedron 58 (2002) 3329
(2002)
Tetrahedron
, vol.58
, pp. 3329
Salvatore, R.N.1
Chu, F.2
Nagle, A.S.3
Kapxhiu, E.A.4
Cross, R.M.5
Jung, K.W.6