| US 7,501,523 B2 | ||
| Method for preparing cucurbiturils | ||
| Anthony Ivan Day, Captains Flat (Australia); Alan Peter Arnold, Flynn (Australia); and Rodney John Blanch, Holt (Australia) | ||
| Assigned to NewSouth Innovations Pty Limited, Sydney, NSW (Australia) | ||
| Appl. No. 10/571,707 PCT Filed Sep. 10, 2004, PCT No. PCT/AU2004/001232 § 371(c)(1), (2), (4) Date Mar. 13, 2006, PCT Pub. No. WO2005/026168, PCT Pub. Date Mar. 24, 2005. |
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| Claims priority of application No. 2003905037 (AU), filed on Sep. 12, 2003. | ||
| Prior Publication US 2007/0066818 A1, Mar. 22, 2007 | ||
| Int. Cl. C07D 403/02 (2006.01) | ||
| U.S. Cl. 548—303.4 | 17 Claims |
| 1. A method for preparing a cucurbituril, the method comprising the steps of:
(a) selecting
(1) a compound of the formula (1)
 wherein:
for each unit of the formula (A)
 in the compound,
R1 and R2 may be the same or different and are each a univalent radical, or
R1, R2 and the carbon atoms to which they are bound together form an optionally substituted cyclic group, or R1 of one unit of the formula (A) and R2 of an adjacent unit of the formula (A) together form a bond or a divalent radical, and
each R3 is independently selected from the group consisting of ═O, ═S, ═NR, ═CXZ, ═CRZ and ═CZ2, where Z is an electron withdrawing group, X is halo and R is H, an optionally substituted straight chain, branched or cyclic,
saturated or unsaturated hydrocarbon radical, or an optionally substituted heterocyclyl radical;
each R5 is independently selected from the group consisting of H, alkyl and aryl;
R7 and R8 may be the same or different and are independently selected from the group consisting of H and —CHR5OR5, or R7 and R8 together form the group —CHR5—O—CHR5, where each R5 is independently selected from the group consisting of H, alkyl and aryl;
R9 and R10 may be the same or different and are independently selected from the group consisting of H and —CHR5OR5, or R9 and R10 together form the group —CHR5—O—CHR5, where each R5 is independently selected from the group consisting of H, alkyl and aryl; and
x is an integer from 1 to 10; and
(2) one or more compounds of the formula (2)
 wherein:
for each unit of the formula (A)
 in the compound,
R1 and R2 may be the same or different and are each a univalent radical, or
R1, R2 and the carbon atoms to which they are bound together form an optionally substituted cyclic group, or R1 of one unit of the formula (A) and R2 of an adjacent unit of the formula (A) together form a bond or a divalent radical, and
each R3 is independently selected from the group consisting of ═O, ═S, ═NR, ═CXZ, ═CRZ and ═CZ2, where Z is an electron withdrawing group, X is halo and R is H, an optionally substituted straight chain, branched or cyclic,
saturated or unsaturated hydrocarbon radical, or an optionally substituted heterocyclyl radical;
each R5 is independently selected from the group consisting of H, alkyl and aryl;
R11 and R12 may be the same or different and are independently selected from the group consisting of H and —CHR5OR5, or R11 and R12 together form the group —CHR5—O—CHR5—, where each R5 is independently selected from the group consisting of H, alkyl and aryl;
R13 and R14 may be the same or different and are independently selected from the group consisting of H and —CHR5OR5, or R13 and R14 together form the group —CHR5—O—CHR5—, where each R5 is independently selected from the group consisting of H, alkyl and aryl; and
y is 0 or an integer from 1 to 9 and x+y=10 or less;
(b) mixing the compound of formula (1), the one or more compounds of formula (2) and an acid to form a mixture; and
(c) exposing the mixture to conditions effective for the compound of the formula (1) and the one or more compounds of the
formula (2) to form a cucurbit[n]uril.
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