Patent GB-1105181-A (GB)
Title: Norbornene compounds
IPC: C07D213/89
Filed: 1965-03-09
Abstract: Plastics such as polystyrene, polyethylene, polypropylene, polymethacrylates, polyacrylamides, polyacrylonitrile, polyamides and polyesters are protected against U.V. by incorporation of 5 - (R - R1 - R2 - methyl) - 7 - (R3 - R4 - methylene) - (R)6 - 5 - norbornene - 2,3 - dicarboximides of formula <FORM:1105181/C3/1> and the corresponding 2,3-dicarboxylic acids, anhydrides, C1- 8 alkyl esters, amides and monoamide-mono-C1- 8 alkyl esters, and acid addition salts and quaternary ammonium compounds thereof, and amine oxides of those compounds containing a basic nitrogen atom in a heteroaryl ring; R being hydrogen or hydroxy; R1 and R3 each being C1- 8 alkyl, phenyl, halophenyl, nitrophenyl, pyridyl or quinolyl provided that R is not H when R1 is alkyl; R2 and R3 each being phenyl, halophenyl, nitrophenyl, pyridyl or quinolyl; R6 being H, C1- 8 alkyl or halogen; R5 being H, C1- 8 alkyl, cycloalkyl, C1- 8 alkenyl, phenyl, C1- 8 alkoxy-C1- 8 alkyl, di-(C1- 8 alkyl)-amino-C1- 8 alkyl, di-(C1- 8 alkyl)-aminocarbonyl-C1- 8 alkyl, cyclic amino-C1- 8 alkyl, phenyl-C1- 8-alkyl.ALSO:The invention comprises 5-(R-R1-R2-methyl) - 7 - (R3-R4 - methylene) - (R)6 - 5 - norbornene-2,3-dicarboximides of formula <FORM:1105181/C2/1> and the corresponding 2,3-dicarboxylic acids, anhydrides, C1- 8 alkyl esters, amides and mono-amide-mono-C1- 8 alkyl esters, and acid addition salts and quaternary ammonium compounds thereof, and amine oxides of those compounds containing a basic nitrogen atom in a heteroaryl ring; R being hydrogen or hydroxy; R1 and R3 each being C1- 8 alkyl, phenyl, halophenyl, nitrophenyl, pyridyl or quinolyl provided that R is not H when R1 is alkyl; R2 and R3 each being phenyl, halophenyl, nitrophenyl, pyridyl or quinolyl; R6 being H, C1- 8 alkyl or halogen; R5 being H, C1- 8 alkyl, cycloalkyl, C1- 8 alkenyl, phenyl, C1- 8 alkoxy-C1- 8 alkyl, di (C1- 8 alkyl) amino-C1- 8 alkyl, di (C1- 8 alkyl) -aminocarbonyl-C1- 8 alkyl, cyclic amino-C1- 8 alkyl, phenyl-C1- 8 alkyl. Preparative methods involve condensing a fulvene of formula <FORM:1105181/C2/2> with an R6-substituted-maleimide or -maleic anhydride followed where necessary by converting R5, opening the ring, esterifying, forming salts, or oxidation to N-oxides.  3 - (a - Hydroxy - a  - 2 - pyridyl) ethyl - 6 - (2-pyridyl) - 6 - methyl fulvene is prepared from cyclopentadienyl-sodium and 2-acetylpyridine.  2 - Benzoylpyridine - N - oxide is prepared by the action of H2O2 on 2-benzoylpyridine and reacted with cyclopentadiene/NaOEt to give a  - phenyl - a  - [6 - phenyl - 6 - (2 - pyridyl - N - oxide) - 2 - fulvenyl] - 2 - pyridine - N - oxide methanol.ALSO:Rodenticidal compositions comprise 5-(R-R1 - R2 - methyl) - 7 - (R3 - R4 - methylene) - (R)6 - 5 - norbornene - 2, 3 - dicarboximides of formula <FORM:1105181/A5-A6/1> and the corresponding 2,3 - dicarboxylic acids, anhydrides, C1-8 alkyl esters, amides and monoamide-mono-C1-8 alkyl esters, and acid addition salts and quaternary ammonium compounds thereof, and amine oxides of those compounds containing a basic nitrogen atom in a heteroaryl ring; R being hydrogen or hydroxy; R1 and R3 each being C1-8 alkyl, phenyl, halophenyl, nitrophenyl, pyridyl or quinolyl provided that R is not H when R1 is alkyl; R2 and R3 each being phenyl, halophenyl, nitrophenyl, pyridyl or quinolyl; R6 being H, C1-8 alkyl or halogen; R5 being H, C1-8 alkyl, cycloalkyl, C1-8 alkenyl, phenyl, C1-8 alkoxy-C1-8 alkyl, di(C1-8 alkyl) amino-C1-8 alkyl, di(C1-8 alkyl)-aminocarbonyl-C1-8 alkyl, cyclic amino-C1-8 alkyl, phenyl-C1-8 alkyl.  The above compounds also have antiarrhythmic activity, e.g. on intravenous injection, and may be used as sun-screening agents in salves and ointments.