Synthesis of biguanidines and triazines, and biguanidino-aluminium complexes as intermediates
View Patent ↗Compounds of formula (I) or salts thereof, in which R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , X and Y are defined as in claim 1 , can be prepared by a process characterized in that a compound of the formula (II) or a salt thereof, is reacted to a compound of the formula (III) or a salt thereof, and an aluminium(III) source, optionally, in the presence of a protic additive or solvent selected from the group consisting of alcohols or amines. The compounds (I) are suitable to be used for the preparation of heterocyclic compounds corresponding to (I) where the group Al(X)(Y) is replaced with an optionally substituted carbon atom, or s-triazine derivatives thereof.
1. A compound of formula (Ia),the formula (Ia) being represented by:
wherein:
R 1 and R 2 are defined as follows:
R 1 is:
(C 1 -C 18 )alkyl, (C 2 -C 18 )alkenyl, or (C 2 -C 18 )alkenyl; or
a group of the formula A 1 ; and
R 2 is:
H, (C 1 -C 18 )alkenyl, (C 2 -C 18 )alkenyl or (C 2 -C 18 )alkynyl; or
a group of the formula A 2 ; or
R 1 and R 2 together with the N-atom, linked to each other form a N-heterocyclic ring having 3 to 7 ring atoms and optionally having one or more additional hetero atoms selected from the group consisting of N, O, and S;
wherein:
R 3 and R 4 are defined as follows:
R 3 is:
H, (C 1 C 18 )alkyl, (C 2 -C 18 )alkenyl, or (C 2 -C 18 )alkynyl; or
a group of the formula A 3 ; and
R 4 is:
H(C 1 -C 18 )alkyl, (C 2 -C 18 )alkenyl, or (C 2 -C, 18 )alkynyl; or
a group of the formula A 4 ; or
R 3 and R 4 together with the N-atom linked to each other form a N-heterocyclic ring having 3 to 7 ring atoms and optionally having one or more additional hetero atoms selected from the group consisting of N, O, and S; and
wheren:
A 1 , A 2 ,A 3 , and A 4 , independently of one another, are (C 3-C 9 )cycloalkyl, (C 4 -C 9 )cycloalkenyl, (C 7 -C 9 )cycloalkynyl, aryl, or heterocyclyl as a basic cyclic moiety;
wherein:
Y is selected from the group consisting of:
(iv) (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 1 -C 4 )alkoxy, (C1-C 4 )alkoxy, and (C 1 -C 4 )alkylthio.
2. A process for preparing a compound of formula (Ia) or a salt thereof according to claim 1 , where the formula (Ia) is represented by:
in which R 1 to R 4 and Y are as defined in claim 1 for formula (Ia);
wherein the method comprises:
reacting a compound (an amine) of the formula (II) or a salt thereof, with a compound of the formula (IIIa) or a salt thereof, and an aluminium(III) source, in the presence of a protic additive or solvent;
wherein the formula (II) is represented by:
in which R 1 and R 2 are defined as in the compound of formula (Ia) to be prepared;
wherein the formula (IIIa) is represented by:
in which R 3 and R 4 are defined as in the compound of formula (Ia) to be prepared;
wherein the aluminium(III) source is selected from:
(i) aluminium salts of the formula (IV):
which:
Y is as defined in the compound of formula (Ia) to he prepared; and
X and Z are the same as Y; and
wherein the protic additive or solvent is X—H, Y—H, or Z—H;
wherein each of X, Y, and Z are defined as set forth in formula (IV).