Polycyclic diiminooxadiazinones
The invention relates to polycyclic diiminooxadiazinones of the formula I and/or of the formula II, in which in each case R 1 to R 12 are each independently hydrogen, a saturated or unsaturated, linear or branched, aliphatic or cycloaliphatic organic radical having 1 to 20 carbon atoms, which is unsubstituted or is substituted by radicals inert to isocyanate groups, and/or comprises heteroatoms inert to isocyanate groups in the chain, or are an aromatic organic radical having 6 to 20 carbon atoms, which is unsubstituted or is substituted by radicals inert to isocyanate groups, wherein two or more of the aforementioned radicals R 1 to R 6 may form further rings, in each case with one another and incorporating one, two or three carbon atoms of the fused ring segment X, and/or two or more of the aforementioned radicals R 7 to R 12 may form further rings, in each case with one another and incorporating one, two or three carbon atoms of the fused ring segment Y.
1. A polycyclic diiminooxadiazinone of the formula I or of the formula II,
in which in each case
R 1 to R 12 are each independently hydrogen, a saturated or unsaturated, linear or branched, aliphatic or cycloaliphatic organic radical having 1 to 20 carbon atoms, which is unsubstituted or is substituted by radicals inert to isocyanate groups, and/or comprises heteroatoms inert to isocyanate groups in the chain, or are an aromatic organic radical having 6 to 20 carbon atoms, which is unsubstituted or is substituted by radicals inert to isocyanate groups,
wherein two or more of the aforementioned radicals R 1 to R 6 may form further rings, in each case with one another and incorporating one, two or three carbon atoms of the fused ring segment X, and/or two or more of the aforementioned radicals R 7 to R 12 may form further rings, in each case with one another and incorporating one, two or three carbon atoms of the fused ring segment Y.
2. The polycyclic diiminooxadiazinone according to claim 1 , wherein
R 1 to R 12 are each independently hydrogen, a saturated or unsaturated, linear or branched, aliphatic or cycloaliphatic organic radical having 1 to 10 carbon atoms, which is unsubstituted or is substituted by radicals inert to isocyanate groups, and/or comprises heteroatoms inert to isocyanate groups in the chain, or are an aromatic organic radical having 6 to 12 carbon atoms, which is unsubstituted or is substituted by radicals inert to isocyanate groups,
wherein two or more of the aforementioned radicals R 1 to R 6 may form further rings, in each case with one another and incorporating one, two or three carbon atoms of the fused ring segment X, and/or two or more of the aforementioned radicals R 7 to R 12 may form further rings, in each case with one another and incorporating one, two or three carbon atoms of the fused ring segment Y.
3. The polycyclic diiminooxadiazinone according to claim 1 , wherein R 1 to R 12 are each independently hydrogen or C 1 -C 10 -alkyl(ene).
4. The polycyclic diiminooxadiazinone according to claim 1 , wherein the heteroatoms inert to isocyanate groups are oxygen, sulfur, tertiary nitrogen and/or quaternary silicon, wherein the substituents on the nitrogen and silicon are inert to isocyanate groups.
5. A polycyclic diiminooxadiazinone of the formula III or of the formula IV,
in which in each case
R 1 , R 3 , R 4 , R 6 , R 7 , R 9 , R 10 and R 12 are each independently hydrogen, a saturated or unsaturated, linear or branched, aliphatic or cycloaliphatic organic radical having 1 to 20 carbon atoms, which is unsubstituted or is substituted by radicals inert to isocyanate groups, and/or comprises heteroatoms inert to isocyanate groups in the chain, or are an aromatic organic radical having 6 to 20 carbon atoms, which is unsubstituted or is substituted by radicals inert to isocyanate groups, and
R 13 to R 24 are each independently hydrogen, a saturated or unsaturated, linear or branched, aliphatic or cycloaliphatic organic radical having 1 to 20 carbon atoms, which is unsubstituted or is substituted by radicals inert to isocyanate groups, and/or comprises heteroatoms inert to isocyanate groups in the chain, or are an aromatic organic radical having 6 to 20 carbon atoms, which is unsubstituted or is substituted by radicals inert to isocyanate groups,
wherein two or more of the aforementioned radicals R 1 , R 3 , R 4 , R 6 , R 13 to R 18 may form further rings in each case with one another and/or two or more of the aforementioned radicals R 7 , R 9 , R 10 , R 12 , R 19 to R 24 may form further rings in each case with one another.
6. A method for preparing a polycyclic diiminooxadiazinone according to claim 1 , wherein at least two diisocyanates, in which the two NCO groups are in a 1,3-position to each other, are cyclized with elimination of CO 2 .
7. The method according to claim 6 , wherein the diisocyanates are cyclized in a first step i) to give a polycyclic iminooxadiazinedione, which
a) is isolated and is converted to the polycyclic diiminooxadiazinone in a further step ii) or
b) is further converted without isolation directly to the polycyclic diiminooxadiazinone in a further step ii).
8. The method according to claim 6 , wherein the cyclization is effected in the presence of at least one catalyst.
9. The method according to claim 8 , wherein the catalyst is a phosphane or a phosphane oxide.
10. The method according to claim 7 , wherein the reaction in step ii) is thermally induced.
11. The method according to claim 6 , wherein the reaction is carried out in the presence of at least one solvent.
12. A composition comprising at least one polycyclic diiminooxadiazinone according to claim 1 and at least one compound comprising one or more Zerevitinoff-active hydrogen atoms.
13. A medicament comprising the polycyclic diiminooxadiazinone according to claim 1 .
14. The polycyclic diiminooxadiazinone according to claim 1 , wherein R 1 to R 12 are each independently hydrogen or C 1 -C 6 -alkyl(ene).
15. The polycyclic diiminooxadiazinone according to claim 1 , wherein R 1 to R 12 are each independently hydrogen or C 1 -C 4 -alkyl(ene).
16. The method according to claim 8 , wherein the catalyst is a compound comprising at least one phosphorus atom in a 5-membered ring.
17. The method according to claim 8 , wherein the catalyst is a phospholane oxide or a phospholene oxide.