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US 2006/0216754 A1Published application
Process for the preparation of ring compounds
AssigneeMerck & Co., Inc.
InventorsDetlef Pauluth, Peer Kirsch, Peter Baeuerle, Oliver Deeg
Life of this patent
Estimating the term…
Abstract
In a process for the preparation of ring compounds via a combinatorial synthesis, the reaction procedure is based on a Suzuki coupling, subsequent halo-demetallation and finally a further Suzuki coupling. The Suzuki couplings are each carried out with a boronic acid or a boronic acid ester. The reaction procedure uses provides novel ring compounds and uses novel synthesis units used for this purpose. The novel ring compounds are suitable for use as constituents in liquid-crystalline mixtures.
Claims17
1-13. (canceled)
A ring compound formula XIII;
- wherein
- m and n, independently of one another, are identical or different and are 0 or 1, and the sum (m+n) is 1 or 2,
- Y is a group of formulae XIV to XVII
- wherein one or two CH groups in the aromatic ring systems may be replaced by N,
- X is a single bond, —CH2—CH2—, —CH═CH—, —C═C— or
- L, independently of one another, are identical or different and are R, F, Cl, Br, I, OH, OR, SH, SR, CN, NO2, NO, CHO, COOH, COOR, CONH2, CONHR, CONR2, CF3, NH2, NHR or NR2,
- R is an alkyl, alkenyl or acyl group having from 1 to 12 carbon atoms or an aryl group having 6 carbon atoms, which is optionally substituted by an alkyl group having from 1 to 12 carbon atoms,
- a, b, c, d, e and f, independently of one another, are identical or different and are 0, 1 or 2, and the sum (a+b+c+d+e+f) is 1 to 8,
- R1 and R2, independently of one another, are identical or different and are H, F, Cl, CN, NCS, a straight-chain or branched, optionally chiral, alkyl radical or alkoxy radical having from 1 to 12 carbon atoms or an alkenyl radical or alkynyl radical having from 2 to 8 carbon atoms, in each of which, in addition, one CH2 group may be replaced by —O—, —CO—, —O—CO—, or —COO— in such a way that heteroatoms are not linked directly to one another and/or one or more H may be replaced by halogen, and
- in the case where m is 0 or n is 0 in R1 or R2, one CH2 group may be replaced by one of the following groups:
- a) trans-1,4-cyclohexylene, in which, in addition, one or more non-adjacent CH2 groups may be replaced by —O— and/or —S—,
- b) a radical from the group consisting of 1,4-bicyclo[2.2.2]octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl and 1,2,3,4-tetrahydronaphthalene-2,6-diyl, or
- c) 1,4-cyclohexenylene,
- and in which the radicals a), b) and c) are optionally substituted by CN, halogen, or combinations thereof.
11 more elements
A compound of formula XIX:
- wherein
- one or two CH groups in the aromatic ring system may be replaced by N:
- r is 0 or 1;
- R is H, F, Cl, CN, NCS, a straight-chain or branched, optionally chiral, alkyl radical or alkoxy radical having from 1 to 12 carbon atoms or an alkenyl radical or alkynyl radical having from 2 to 8 carbon atoms, in each of which, in addition, one CH2 group may be replaced by —O—, —CO—, —O—CO— or —COO— in such a way that heteroatoms are not linked directly to one another and/or one or more H may be replaced by halogen, and
- in the case where r is =0, one CH2 group in R may be replaced by one of the following groups:
- a) trans-1,4-cyclohexylene, in which, in addition, one or more non-adjacent CH2 groups may be replaced by —O— and/or —S—,
- b) a radical from the group consisting of 1,4-bicyclo[2.2.2]octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl and 1,2,3,4-tetrahydronaphthalene-2,6-diyl, or
- c) 1,4-cyclohexenylene,
- and in which the radicals a), b) and c) may also be substituted by CN, halogen, or combinations thereof,
- L is R′, F, Cl, Br, I, OH, OR′, SH, SR′, CN, NO2, NO, CHO, COOH, COOR′, CONH2, CONHR′, CONR′2, CF3, NH2, NHR′ or NR′2;
- R′ is an alkyl, alkenyl or acyl group having from 1 to 12 carbon atoms or an aryl group having 6 carbon atoms, which is optionally substituted by an alkyl group having from 1 to 12 carbon atoms;
- a is 0, 1 or 2, and
- R6 and R7, independently of one another, are identical or different and are H, C1-C12-alkyl, C2-C2-alkenyl or aryl, and where R6 and R7 may also be bridged in a cyclic manner.
10 more elements
A compound of formula XXI:
- wherein
- one or two CH groups in the aromatic ring system may be replaced by N;
- r is 0 or 1:
- R3, R4 and R5, independently of one another, are identical or different and are H, C1-C12-alkyl or C1-C12-alkoxy;
- R6 and R7, independently of one another, are identical or different and are H, C1-C12-alkyl, C2-C12-alkenyl or aryl, and where R6 and R7 may also be bridged in a cyclic manner:
- M is Si, Ge or Sn;
- L is R′, F, Cl, Br, I, OH, OR′, SH, SR′, CN, NO2, NO, CHO, COOH, COOR′, CONH2, CONHR′, CONR′2, CF3, NH2, NHR′ or NR′2;
- R′ is an alkyl, alkenyl or acyl group having from 1 to 12 carbon atoms or an aryl group having 6 carbon atoms, which is optionally substituted by an alkyl group having from 1 to 12 carbon atoms;
- and
- a is 0, 1 or 2.
7 more elements
Dependencies are inferred from the claim text.