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Synlett 2006(1): 0049-0052  
DOI: 10.1055/s-2005-922761
LETTER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Novel Molecular Clips Based on Diethoxycarbonyl Glycoluril

Guodong Yina, Zhiguo Wanga, Yunfeng Chena, Anxin Wu*a, Yuanjiang Pan*b
a Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, Central China Normal University, Wuhan 430079, P. R. of China
e-Mail: chwuax@mail.ccnu.edu.cn;
b Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China
e-Mail: panyuanjiang@zju.edu.cn;
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Publikationsverlauf

Received 26 September 2005
Publikationsdatum:
16. Dezember 2005 (online)

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Abstract

A novel class of molecular clips was synthesized, which are soluble in most non-polar organic solvents. Aromatic amines and diethoxycarbonyl glycoluril were used for the first time in this type of reaction. All reaction products gave satisfying 1H NMR, 13C NMR, MS, and IR spectra. In addition, the structure and conformation of 4d were confirmed by single crystal X-ray diffraction.

Key words

molecular clips - diethoxycarbonyl glycoluril - aromatic amines - synthetic receptors - conformers

    References and Notes

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22

Compound 4a: IR (KBr): 3457 (m), 2850 (m), 1762 (s), 1731 (s), 1464 (m), 1419 (m), 1389 (m), 1251 (s), 1173 (m), 1054 (m), 950 (m), 761 (m), 699 (m) cm-1. 1H NMR (400 MHz, CDCl3): δ = 7.12 (t, 4 H), 6.94-6.88 (m, 6 H), 5.49 (d, 4 H, J = 13.2 Hz), 4.56 (d, 4 H, J = 13.2 Hz), 4.33 (q, 4 H, J = 6.8 Hz), 1.35 (t, 6 H, J = 6.8 Hz). 13C NMR (100 MHz, CDCl3): δ = 165.13, 157.32, 145.86, 129.24, 121.71, 117.73, 76.13, 63.33, 58.31, 13.84. MS: m/z (%) = 521 (100) [M+], 416 (68), 387 (95), 343 (61), 240 (31), 105 (93).
Compound 4b: IR (KBr): 3456 (m), 2861 (m), 1763 (s), 1731 (s), 1522 (m), 1465 (m), 1418 (m), 1392 (m), 1247 (s), 1176 (m), 1052 (m), 944 (m), 809 (m) cm-1. 1H NMR (400 MHz, CDCl3): δ = 6.92 (d, 4 H), 6.83 (d, 4 H), 5.43 (d, 4 H, J = 13.2 Hz), 4.53 (d, 4 H, J = 13.2 Hz), 4.32 (q, 4 H, J = 6.8 Hz), 2.24 (s, 6 H), 1.34 (t, 6 H, J = 6.8 Hz). 13C NMR (100 MHz, CDCl3): δ = 165.18, 157.30, 143.58, 130.92, 129.73, 117.92, 76.09, 63.26, 58.51, 20.44, 13.81. MS: m/z (%) = 549 (100) [M+], 400(91), 356 (41), 118 (88).
Compound 4c: IR (KBr): 3453 (m), 2919 (m), 2847 (m), 1765 (s), 1727 (s), 1465 (m), 1412 (m), 1384 (m), 1248 (s), 1158 (m), 1057 (m), 936 (m), 782 (m), 701 (m) cm-1. 1H NMR (400 MHz, CDCl3): δ = 7.04 (2 H), 6.80-6.72 (m, 6 H), 5.46 (d, 4 H, J = 13.2 Hz), 4.51 (d, 4 H, J = 13.2 Hz), 4.33 (q, 4 H, J = 7.2 Hz), 2.20 (s, 6 H), 1.35 (t, 6 H, J = 7.2 Hz). 13C NMR (100 MHz, CDCl3): δ = 165.22, 157.44, 145.98, 139.00, 128.98, 122.84, 118.81, 115.03, 76.09, 63.34, 58.68, 21.44, 13.87. MS: m/z (%) = 549 (100) [M+], 400(97), 356 (49), 118 (60).
Compound 4d: IR (KBr): 3451 (s), 2987 (m), 2939 (m), 1768 (s), 1729 (s), 1515 (s), 1463 (m), 1416 (m), 1284 (m), 1242 (s), 1179 (m), 1032 (m), 824 (m) cm-1. 1H NMR (400 MHz, CDCl3): δ = 6.93 (d, 4 H, J = 8.8 Hz), 6.71 (d, 4 H, J = 8.8 Hz), 5.34 (d, 4 H, J = 12.8 Hz), 4.53 (d, 4 H, J = 12.8 Hz), 4.33 (q, 4 H, J = 7.2 Hz), 3.73 (s, 6 H), 1.34 (t, 6 H, J = 7.2 Hz). 13C NMR (100 MHz, CDCl3): δ = 165.21, 157.48, 154.91, 139.73, 120.12, 114.40, 76.05, 63.27, 59.32, 55.20, 13.83. MS: m/z (%) = 581 (100)[M+], 416 (41), 372 (26), 191 (27), 176 (30), 134 (99), 120 (71).
Compound 4e: IR (KBr): 3457 (m), 2962 (m), 1753 (s), 1737 (s), 1261 (s), 1093 (s), 1050 (s), 802 (s) cm-1. 1H NMR (400 MHz, CDCl3): δ = 7.05 (d, 4 H, J = 8.8 Hz), 6.90 (d, 4 H, J = 8.8 Hz), 5.41 (d, 4 H, J = 12.8 Hz), 4.49 (d, 4 H, J = 12.8 Hz), 4.33 (q, 4 H, J = 7.2 Hz), 2.78-2.82 (m, 2 H), 1.34 (d, 6 H, J = 7.2 Hz), 1.18 (d, 12 H, J = 2.4 Hz). 13C NMR (100 MHz, CDCl3): δ = 165.32, 157.63, 144.01, 142.63, 127.13, 118.49, 76.14, 63.33, 59.20, 33.21, 23.95, 13.92. MS: m/z (%) = 605 (100) [M+], 428 (74), 385 (45), 287 (28), 202 (28), 146 (40), 132 (83).
Compound 4f: IR (KBr): 3411 (s), 1765 (s), 1722 (s), 1498 (m), 1468 (m), 1415 (s), 1238 (s), 1048 (m), 903 (m), 833 (m), 717 (m) cm-1. 1H NMR (400 MHz, CDCl3): δ = 7.02 (d, 4 H, J = 8.8 Hz), 6.82 (d, 4 H, J = 8.8 Hz), 5.48 (d, 4 H, J = 14.0 Hz), 4.62 (d, 4 H, J = 14.0 Hz), 4.33 (q, 4 H, J = 7.2 Hz), 1.35 (t, 6 H, J = 7.2 Hz). 13C NMR (100 MHz, CDCl3): δ = 164.93, 157.10, 144.22, 129.21, 126.47, 118.46, 76.20, 63.53, 57.61, 13.87. MS: m/z (%) = 590 (100) [M+], 538 (21), 420 (70), 376 (27), 202 (25), 191 (9), 189 (21), 145 (65).
Compound 4g: IR (KBr): 3448 (m), 2981 (w), 2936 (w), 1746 (s), 1726 (s), 1496 (m), 1467 (m), 1417 (m), 1280 (m), 1239 (s), 1094 (m), 1047 (m), 975 (m), 908 (m), 818 (m) cm-1. 1H NMR (400 MHz, CDCl3): δ = 7.18 (d, 4 H, J = 8.8 Hz), 6.77 (d, 4 H, J = 8.8 Hz), 5.48 (d, 4 H, J = 14.0 Hz), 4.62 (d, 4 H, J = 14.0 Hz), 4.34 (q, 4 H, J = 7.2 Hz), 1.35 (t, 6 H, J = 7.2 Hz). 13C NMR (100 MHz, CDCl3): δ = 164.87, 157.04, 144.77, 132.15, 118.88, 113.93, 76.16, 63.51, 57.53, 13.86. MS: m/z (%) = 679 (73) [M+], 467 (58), 466 (10), 464 (66), 423 (30), 420 (26), 409 (4), 243 (10), 241 (24), 240 (63), 182 (100).
Compound 4h: IR (KBr): 3426 (m), 1749 (s), 1727 (s), 1493 (m), 1466 (m), 1417 (m), 1279 (m), 1245 (s), 1174 (m), 1093 (m), 909 (m), 812 (m), 694 (m) cm-1. 1H NMR (400 MHz, CDCl3): δ = 7.37 (d, 4 H, J = 7.6 Hz), 6.66 (d, 4 H, J = 7.6 Hz), 5.47 (d, 4 H, J = 14.0 Hz), 4.61 (d, 4 H, J = 14.0 Hz), 4.33 (q, 4 H, J = 7.2 Hz), 1.34 (t, 6 H, J = 7.2 Hz). 13C NMR (100 MHz, CDCl3): δ = 164.95, 157.11, 145.62, 138.20, 119.46, 84.29, 76.24, 63.56, 57.62, 13.94. MS: m/z (%) = 723 (93) [M+], 647 (13), 513 (70), 387 (18), 231 (100), 208 (48).