References
1
Smeets JWH.
Sijbesma RP.
Niele FGM.
Spek AL.
Smeets WJJ.
Nolte RJM.
J. Am. Chem. Soc.
1987,
109:
928
2
Creaven BS.
Gallagher JF.
McDongh JP.
McGinley J.
Murray BA.
Whelan GS.
Tetrahedron
2004,
60:
137
3
Philp D.
Stoddart JF.
Angew. Chem., Int. Ed. Engl.
1996,
35:
1155
4
Lehn JM.
In Superamolecular Chemistry
VCH;
New York:
1995.
5
Elemans JAAW.
Slangen RRJ.
Rowan AE.
Nolte RJM.
J. Org. Chem.
2003,
68:
9040
6
Lutzen A.
Starnes SD.
Rudkevich DM.
Rebek J.
Tetrahedron Lett.
2000,
41:
3777
7
Sijbesma RP.
Kentgens APM.
Lutz ETG.
Maas JH.
Nolte RJM.
J. Am. Chem. Soc.
1993,
115:
8999
8
Compound 3a: 1H NMR (300 MHz, DMSO-d
6): δ = 9.37 (s, 2 H, OH) and 8.32 (s, 2 H, OH), 7.08 (s, 10 H, ArH), 6.97 (d, 2 H, ArH, J = 8.4 Hz) and 6.48 (d, 2 H, ArH, J = 8.4 Hz), 5.36 and 3.59 (d, 4 H, ArCH2N, J = 15.9 Hz), 4.50 and 3.91 (d, 8 H, ArCH2N, J = 15.9 Hz). 13C NMR (75 MHz, DMSO-d
6): δ = 159.50, 159.06 (urea C=O), 145.24, 143.71, 138.47, 134.90, 134.33, 128.64, 128.53, 128.35, 128.17, 125.18, 113.30, 85.25, 78.73, 45.76, 45.34, 44.94, 37.05. ESI-MS (FAB): m/z = 563 [M + H]+; mp >294 °C. Compound 3b: 1H NMR (CDCl3): δ = 7.08 (s, 10 H, ArH), 6.69 (d, 2 H, ArH, J = 8.4 Hz) and 6.63 (d, 2 H, ArH, J = 8.4 Hz), 5.54 and 3.80 (d, 4 H, ArCH2N, J = 15.9 Hz), 4.72 and 4.09 (d, 4 H, ArCH2N, J = 15.9 Hz), 3.91 (s, 6 H, OCH3) and 3.78 (s, 6 H, OCH3). 13C NMR (75 MHz, CDCl3): δ = 157.70, 157.27 (urea C=O), 151.98, 146.58, 133.80, 131.14, 130.09, 128.73, 128.32, 128.25, 124.98, 110.55, 85.63, 62.50, 61.56, 60.79, 56.31, 56.07, 46.00, 45.78, 38.10. ESI-MS (FAB): m/z = 619 [M + H]+; mp >294 °C. Compound 3c: 1H NMR (CDCl3):
δ = 7.08 (s, 10 H, ArH), 6.91 (d, 2 H, ArH, J = 8.4 Hz) and 6.59 (d, 2 H, ArH, J = 8.4 Hz), 5.59 and 3.76 (d, 4 H, ArCH2N, J = 15.9 Hz), 4.70 and 4.08 (d, 4 H, ArCH2N, J = 15.9 Hz), 4.13 (q, 4 H, OCH2C, J = 10.9 Hz), 3.96 (q, 4 H, OCH2C, J = 10.9 Hz), 1.47-1.37 (br, 12 H, OCCH3). 13C NMR (75 MHz, CDCl3): δ = 158.07, 157.68 (urea C=O), 151.67, 146.49, 134.17, 131.31, 130.19, 128.78, 128.71, 128.51, 128.41, 124.79, 111.68, 85.48, 69.45, 64.17, 45.50, 37.83, 16.06, 15.22. ESI-MS (FAB): m/z = 675 [M + H]+; mp 227.4-228.1 °C.
9
iii) has been obtained by Nolte et al. by using SnCl4 as a catalyst, the 1H NMR spectrum of 3b show much difference form that of iii). See: Sijbesma RP.
Nolte RJM.
Recl. Trav. Chim. Pays-Bas
1993,
112:
643
10
Isaacs L.
Witt D.
Lagona J.
Org. Lett.
2001,
3:
3221
11
Wu A.
Chakraborty A.
Witt D.
Lagona J.
Damkaci F.
Ofori MA.
Chiles JK.
Fettinger JC.
Isaacs L.
J. Org. Chem.
2002,
67:
5817