Synthesis of tripodal catechol derivatives with an adamantyl base for functionalising surfaces

摘要

Tripodal catechol derivatives having adamantyl skeleton (I) are new. Tripodal catechol derivatives having adamantyl skeleton of formula (I) are new. Y1 : CH 2-, -CH=CH-, -CC-, -O-, -S-, -S-S-, -NH-, -O-NH-, -NH-O-, -HC=N-O-, -O-N=CH-, -NR1-, -(hetero)aryl-, -(C=O)-, -O-(C=O)-, -C(=O)-O-, -NH-C(=O)-, -C(=O)-NH-, -NR1-C(=O)-, -C(=O)-NR1-, -NH-C(=O)-NH- or -NH-C(=S)-NH-; R1 : linear 1-10C-alkyl or branched or cyclic 3-10C-alkylsteht; Z : dihydroxyphenyl group of formula (a1), (E)-2-(3,4-dihydroxyphenyl)vinyl or tetrahydro-isoquinoline-6,7-diol group of formula (a2); R2 : -H, -OH or -COOH; R3 : H or OH; A : no atom or -C(=O)-; R4 : H or 3,4-dihydroxyphenyl-methyl; X : -(CH 2) p-R5, or branched 3-10C-alkyl, branched 3-10C-alkenyl, branched 3-10C-alkynyl, cyclic 3-10C-alkyl, cyclic 3-10C-alkenyl, cyclic 3-10C-alkynyl, (hetero)aryl, where if X is branched alkyl, alkenyl and alkynyl group, a cyclic alkyl or alkenyl group or (hetero)aryl then carbon atoms of these groups are optionally contains R5; R5 : H, -NH 2, -NO 2, -OH, -SH, -O-NH 2, -NH-NH 2, -N=C=S, -NC=O, -CH=CH 2, -CCH, -COOH, -(C=O)H, -(C=O)R6, where the hydroxy-, thio-, amino- or C=O-groups are optionally protected by a protecting group, -N 3, -OR6, -COOR6, -NHR6, - NR6R7, -CO-NHR6, -CONR6R7, -NH-CO-R6 or 4-(2,5-dioxopyrrol-1-yl); R6, R7 : linear 1-10C-alkyl, linear 2-10C-alkenyl, linear 2-10C-alkynyl, branched 3-10C-alkyl, branched 3-10C-alkenyl, branched 3-10C-alkynyl, cyclic 3-10C-alkyl or cyclic 3-10C-alkenyl; and m, n, p : 0-10. Independent claims are included for: (1) the preparation of (I); and (2) use of (I) in a method for the functionalization of surfaces, where the functionalization is carried by dipping and rinsing. [Image] [Image].