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A good illustration of this concept is the constrained analogue of LHRH (see ref 7) by Freidinger: Freidinger, R. M.; Veber, D. F.; Perlow, D. S.; Brooke, J. R.; Saperstein, R. Science 1980, 210, 656-658.
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See also ref 4. For recent examples, see: (a) Palomo, C.; Aizpurua, J. M.; Benito, A.; Miranda, J. I.; Fratila, R. M.; Matute, C.; Domercq, M.; Gago, F.; Martin-Santamaria, S.; Linden, A. J. Am. Chem. Soc. 2003, 125, 16243-16260.
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64549112943
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LHRH: luteinizing hormone-releasing hormone
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LHRH: luteinizing hormone-releasing hormone.
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(a) Freidinger, R. M.; Veber, D. F.; Hirschmann, R.; Paege, L. M. Int. J. Pent. Protein Res. 1980, 76, 464-470.
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Golebiowski, A.; Jozwik, J.; Klopfenstein, S. R.; Colson, A.-O.; Grieb, A. L.; Russell, A. F.; Rastogi, V. L.; Diven, C. F.; Portlock, D. E.; Chen, J. J. J. Comb. Chem. 2002, 4, 584-590.
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0035959447
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For a review on β-turn mimetic library synthesis, see
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For a review on β-turn mimetic library synthesis, see: Souers, A. J.; Ellman, J. A. Tetrahedron 2001, 57, 7431-7448.
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(a) Umkehrer, M.; Kalinski, C.; Kolb, J.; Burdack, C. Tetrahedron Lett. 2006, 47, 733-737.
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(c) Maison, W.; Schlemminger, I.; Westerhoff, O.; Martens, J. Bioorg. Med. Chem. 2000, 8, 1343-1360.
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41
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0034191466
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The rather high stability of the carbinolamine and therefore slow formation of the imine most likely explains the long reaction time of this particular Ugi reaction and the formation of side products such as the iminoimidazolidine
-
(b) Atherton, J. H.; Brown, K. H.; Crampton, M. R. J. Chem. Soc., Perkin Trans. 2 2000, 941-946. The rather high stability of the carbinolamine and therefore slow formation of the imine most likely explains the long reaction time of this particular Ugi reaction and the formation of side products such as the iminoimidazolidine.
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J. Chem. Soc., Perkin Trans. 2
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Atherton, J.H.1
Brown, K.H.2
Crampton, M.R.3
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42
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0000887411
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There is evidence that pure N-methyleneaniline occurs as a cyclic trimer. However, since nucleophilic species are present the formation of this trimer is not likely. See: Miller, J. G.; Wagner, E. C. J. Am. Chem. Soc. 1932, 54, 3698-3706.
-
There is evidence that pure N-methyleneaniline occurs as a cyclic trimer. However, since nucleophilic species are present the formation of this trimer is not likely. See: Miller, J. G.; Wagner, E. C. J. Am. Chem. Soc. 1932, 54, 3698-3706.
-
-
-
-
43
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64549123843
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3N · HCl was added, the amidine was not present after 77 h and the yield of 15 is 73%. During the reaction, however, 13 was observed onTLC, supporting its involvementas an intermediate.
-
3N · HCl was added, the amidine was not present after 77 h and the yield of 15 is 73%. During the reaction, however, 13 was observed onTLC, supporting its involvementas an intermediate.
-
-
-
-
45
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0348048827
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Keung, W.; Bakir, F.; Patron, A. P.; Rogers, D.; Priest, C. D.; Darmohusodo, V. Tetrahedron Lett. 2004, 45, 733-737.
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Tetrahedron Lett
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Keung, W.1
Bakir, F.2
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Rogers, D.4
Priest, C.D.5
Darmohusodo, V.6
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46
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64549100625
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-
See ref 6a and references therein
-
See ref 6a and references therein.
-
-
-
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47
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0032820462
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Belvisi, L.; Gennari, C.; Mielgo, A.; Potenza, D.; Scolastico, C. Eur. J. Org. Chem. 1999, 389-400.
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Belvisi, L.1
Gennari, C.2
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Potenza, D.4
Scolastico, C.5
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49
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64549155591
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For all data, see Supporting Information
-
For all data, see Supporting Information.
-
-
-
-
50
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64549116226
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-
1H NMR signals (especially for 10). These values are therefore not reliable and were excluded from the table.
-
1H NMR signals (especially for 10). These values are therefore not reliable and were excluded from the table.
-
-
-
-
51
-
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64549118574
-
-
Although the signals for H2 and H3 overlap in the 233-283 K range, it is clear from Figure 5B that the temperature coefficients for both protons are significantly larger than in the 294-330 K range. However, it must be noted that high temperature coefficients are especially observed in the low temperature range, where line broadening (possibly due to aggregation) is observed
-
Although the signals for H2 and H3 overlap in the 233-283 K range, it is clear from Figure 5B that the temperature coefficients for both protons are significantly larger than in the 294-330 K range. However, it must be noted that high temperature coefficients are especially observed in the low temperature range, where line broadening (possibly due to aggregation) is observed.
-
-
-
-
52
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0035915339
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and references therein
-
Cheng, R. P.; Suich, D. J.; Cheng, H.; Roder, H.; DeGrado, W. F. J. Am. Chem. Soc. 2005, 123, 12710-12711, and references therein.
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Cheng, R.P.1
Suich, D.J.2
Cheng, H.3
Roder, H.4
DeGrado, W.F.5
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53
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64549104536
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Partial cleavage of the DMB group took place under acidic conditions, and therefore 1 equiv of acid was used in the reactions using 2,4-dimethoxy- benzylamine.
-
Partial cleavage of the DMB group took place under acidic conditions, and therefore 1 equiv of acid was used in the reactions using 2,4-dimethoxy- benzylamine.
-
-
-
-
54
-
-
64549127272
-
-
2 was added to increase the solubility of the dihydropyridone starting material, since it is very poorly soluble in MeOH.
-
2 was added to increase the solubility of the dihydropyridone starting material, since it is very poorly soluble in MeOH.
-
-
-
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