Aryl substituted bicyclic compounds as herbicides
Disclosed are compounds of Formula 1, including all N-oxides, stereoisomers, and salts thereof, wherein Q 1 , Q 2 , R 1 , R 2 , Y, J and R 7 are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling undesired vegetation comprising contacting the undesired vegetation or its environment with an effective amount of a compound or a composition of the invention.
1. A process for preparing a compound of Formula 1C
comprising reducing a compound of Formula 1 B
in the presence of a nickel catalyst
followed by in-situ cyclization of the resulting amine,
wherein the compound of Formula 1 B is prepared by reacting a compound of Formula 1A
with nitromethane in the presence of a base in ethanol.
2. A process according to claim 1 , wherein the reduction of the compound of Formula 1B is carried out using sodium borohydride in the presence of nickel(II) chloride hexahydrate.
3. A process for preparing a compound of Formula 3C
comprising reducing a compound of Formula 3B
with sodium borohydride in the presence of a nickel catalyst
followed by in-situ cyclization of the resulting amine in methanol.
4. The process of claim 3 wherein the nickel catalyst is nickel(II) chloride hexahydrate.
5. The process of claim 3 wherein the compound of Formula 3B is prepared by reacting 4-trifluoromethylbenzaldehyde with dimethyl malonate.
6. The process of claim 5 wherein the reaction takes place in the presence of piperidine.