Water → (4aR,8aR)-3,3-Dimethyloctahydroquinoxalin-2(1H)-one
Reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH2:8].[CH3:9][C:10]([CH3:14])(O)[C:11]#N.[OH2:15]>>[CH3:9][C:10]1([CH3:14])[NH:8][C@H:3]2[C@@H:2]([CH2:7][CH2:6][CH2:5][CH2:4]2)[NH:1][C:11]1=[O:15]Participants
4
Procedure
The disclosure deals with novel synthesis involving (a) hydrogenation of a cis-3,3-dialkyl-3,4-dihydroquinoxaline-2-one in the presence of a suitable hydrogenation catalyst, at elevated temperature and pressure, to yield a cis-3,3-dialkyl decahydroquinoxaline-2-one; (b) reaction of trans-1,2-diaminocyclohexane with acetone cyanohydrin in the presence of water to yield trans-3,3-dimethyl-decahydroquinoxaline-2-one; and (c) a reaction of 1,2-diamine with a saturated acyclic or cyclic monoketone or aldehyde and a holoform, in the presence of (i) a phase transfer catalyst (ii) an organic solvent, and (iii) solid or aqueous alkali to yield 2-keto-1,4-diazacycloalkanes. Such compounds exhibit exceptional UV light stabilizing property.
Sources & evidence
- ORD record
- ord-d9ef9deefc0843b3822bcbaf9bc53184
- Source dataset
- uspto-grants-1987_12
- Patent number
- US04711957
Reaction notes
Loading…