Substituted 1,2-azaborine heterocycles
View Patent ↗Aromatic heterocycles incorporating boron and nitrogen atoms, in particular, 1,2-azaborine compounds having the formula and their use as synthetic intermediates.
1. An azaborine having the formula
wherein R 1 is hydrogen, deuterium, halogen, alkyl having 1-6 carbons, aryl having 1-carbons, heteroaryl having 1-6 carbons, acyl having 1-6 carbons, alkenyl having 1-6 carbons, alkynyl having 1-6 carbons, sulfonyl, —OR 7 , an amine protecting group, or Si(R 8 ) 3 , where each R 7 is independently hydrogen, alkyl having 1-6 carbons, acyl having 1-6 carbons, alkenyl having 1-6 carbons, tert-butyloxycarbonyl, or sulfonyl, and each R 8 is independently alkyl having 1-6 carbons, aryl having 1-6 carbons, alkoxy having 1-6 carbons, acyl having 1-6 carbons, alkenyl having 1-6 carbons, or tert-butyloxycarbonyl;
R 5 is hydrogen, deuterium, halogen, alkyl having 1-6 carbons, acyl having 1-6 carbons, amide, alkenyl having 1-6 carbons, alkynyl having 1-6 carbons, —OR 7 , hydroxyl, —CN, —SR 7 , sulfonyl, aryl having 1-6 carbons, heteroaryl having 1-6 carbons, or a leaving group LG.
2. The azaborine of claim 1 , wherein R 1 is alkyl having 1-6 carbons.
3. The azaborine of claim 1 , wherein R 1 is tert-butyl.
4. The azaborine of claim 1 , wherein R 1 is Si(R 8 ) 3 .
5. The azaborine of claim 4 , wherein R 1 is —SiMe 2 t-Bu.
6. The azaborine of claim 1 , wherein R 5 is a halogen.
7. The azaborine of claim 1 , wherein R 5 is hydrogen.
8. The azaborine of claim 1 , wherein R 5 is I, Br, Cl, F, OH, OTf or OR 7 .
9. The azaborine of claim 1 , wherein R 1 is alkyl, aryl, vinyl, acyl, BOC, or Si(R 8 ) 3 .
10. The azaborine of claim 1 , wherein R 1 is —SiMe 2 t-Bu and R 5 is Br.
11. The azaborine of claim 1 , wherein R 5 is Br.
12. The azaborine of claim 4 , wherein R 5 is a halogen.
13. The azaborine of claim 9 , wherein R 5 is I, Br, Cl, F, OH, OTf or OR 7 .
14. The azaborine of claim 7 , wherein R 1 is alkyl, aryl, vinyl, acyl, BOC, or Si(R 8 ) 3 .
15. The azaborine of claim 1 , wherein R 1 is tert-butyl.
16. An azaborine having the formula
wherein R 1 is selected from alkyl having 1-6 carbons, aryl having 1-6 carbons, acyl having 1-6 carbons, or Si(R 8 ) 3 , wherein each R 8 is independently alkyl having 1-6 carbons, aryl having 1-6 carbons, alkoxy having 1-6 carbons, acyl having 1-6 carbons, or tert-butyloxycarbonyl; and R 5 is selected from H, Br, Cl, I, F, —OR 7 , wherein each R 7 is independently alkyl having 1-6 carbons, acyl having 1-6 carbons, or tert-butyloxycarbonyl.
17. The azaborine of claim 16 , wherein R 5 is Br, Cl, I, or F.
18. The azaborine of claim 16 , wherein R 1 is —SiMe 2 t-Bu.