Methods for preparing functional tetraazacycloalkane compounds using a specific cyclic bisaminal compound

A compound according to formulae (I) or (II), wherein:

• R1 and R2, identical or different, represent a hydrogen atom, a C1-C4 alkyl group, or, together with the carbon atoms of the bisaminal bridge to which they are linked, form a saturated or unsaturated, six-membered hydrocarbon cyclic group,
• wherein:
• m and n, identical or different, are equal to 0 or to 1;
• A1, A2, A3, A′2, A′3, identical or different, are chosen from the groups CH2, CHR and C═O;
• on condition that A′2 or A′3 designates a CHR group;
• and
• the group or groups R, identical or different, is:
• a hydrocarbon group, saturated or unsaturated, straight or branched, cyclic or acyclic, comprising 1 to 30 carbon atoms, and comprising one or more heteroatoms selected from:
• a group V, V being chosen from amongst a halogen, a nitrile, NR5R6, NO2, OR7, COX, NHCOX, —CONR5R6, (O)sPO(OR8)(OR9), s being an integer ranging from 0 to 1, X being a halogen or a group OR5;
• R5, R6, R7, R8 and R9 being chosen from amongst a hydrogen atom and a straight or branched, saturated or unsaturated C1-C30 alkyl group,
• a group W, wherein W is selected from a monocyclic, bicyclic or tricyclic, saturated or unsaturated cyclic hydrocarbon group with the cycle or cycles comprising 5 to 6 carbon atoms, and at least one of said cycle or cycles being capable of being substituted by one or more groups chosen amongst N-chlorosuccinimide, P(C6H5)2, P(O)(C6H5)2, (CH2)p V, p being an integer ranging from 0 to 4 and/or being capable of forming, with one or more carbon atoms of the cycle, one or more ketone functions,
• a group Y, Y being a heterocyclic group, capable of being monocyclic, bicyclic or tricyclic, saturated or unsaturated, the cycle or cycles comprising five to six members, and at least one of them being capable of being substituted on at least one or more carbon atoms or heteroatoms by one or more groups chosen from amongst the groups V and W, a straight or branched, saturated or unsaturated, C1-C30, alkyl group substituted by one or more groups V and/or W, a trityl group;
• the heterocycle group being capable of forming, with one or more carbon atoms of the cycle, one or more ketone functions,
• a straight or branched saturated or unsaturated C1-C30 alkyl group substituted by one or more groups, V, W, and/or Y
• hydrophobic groups chosen from amongst saturated or unsaturated, straight or branched, cyclic or acylic hydrocarbon groups comprising at least one linear hydrocarbon chain having 8 to 30 carbon atoms,
• hydrophilic groups comprising at least one glycol ethylene group,
• tensioactive groups,
• fluorescent groups,
• ionic groups chosen from amongst organic groups of the guadinidium or arsenium type,
• groups bearing at least one protected or unprotected primary, protected or unprotected secondary or protected or unprotected tertiary amine function,
• groups bearing at least one alcohol function,
• groups bearing at least one alkene and/or alkyne function,
• groups bearing at least one amide function,
• groups bearing at least cyano, nitrile, CF3 function, and
• groups bearing at least one acid, ester, aldehyde function.