Synthesis of tripodal catechol derivatives with a flexible base for functionalising surfaces

摘要

Tripodal catechol derivative (I) is new. Tripodal catechol derivative of formula (Z-Y1-(CH 2) n-C(X)((CH 2) n-Y1-Z)-(CH 2) n-Y1-Z) (I) is new. n, m, p : 0-10; 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 alkyl; Z : catechol derivative of formula (IIa), 3,4-dihydroxyphenyl-ethenylidene or 1,2,3,4-tetrahydro-isoquinoline-6,7-diol derivative of formula (IIb); R2 : -H, -OH or -COOH; R3 : -H or -OH; A : no atom or -(C=O)-; R4 : -H or 3,4-dihydroxyphenyl-methylidene; X : 3-10C alkyl, 3-10C alkenyl, 3-10C alkynyl (all branched), 3-10C alkyl, 3-10C alkenyl, 3-10C alkynyl (all cyclic), (hetero)aryl (where optionally a C atom of X carries R5) or -(CH 2) p-R5; R5 : -H, -NH 2, -NO 2, -OH, -SH, -O-NH 2, -NH-NH 2, -N=C=S-, -N=C=O-, -CH=CH 2, -C=CH, -COOH, -(C=O)H, -(C=O)R6 (where OH, thio, amino or C=O groups may be optionally protected by a protecting group), -N 3, -OR6, -COOR6, -NHR6, -NR6R7, -CO-NHR6, -CONR6R7, -NHCO-R6 or 4-(2,5-dioxopyrrole-1-yl); and R6, R7 : 1-10C alkyl, 2-10C alkenyl, 2-10C alkynyl (all linear), 3-10C alkyl, 3-10C alkenyl, 3-10C alkynyl (all branched), 3-10C alkyl or 3-10C alkenyl (both cyclic). Independent claims are also included for: (1) preparing (I); and (2) use of (I) in a method for functionalizing surfaces by dip-and-rinse method. [Image].