2-arylquinolines and process for producing the same
AssigneesAsahi Glass Company, Limited, The Green Cross Corporation
InventorsTakashi Okazoe, Yoshitomi Morizawa
Life of this patent
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Abstract
2-Arylquinolines represented by formula (1): ##STR1## wherein R.sup.1, R.sup.3 to R.sup.9 each represents hydrogen, halogen, lower alkyl, cyclic lower alkyl, aryl, aralkyl, alkoxy or --C.sub.m F.sub.2m+1 ; R.sup.2 represents hydrogen, halogen, lower alkyl, cyclic lower alkyl, aryl, aralkyl, alkoxy, --C.sub.n F.sub.2n+1 or --CH.sub.2 Q, in which Q represents a monovalent organic group obtained by eliminating from an organic compound having --NH-- the hydrogen atom bonded to the nitrogen, or halogen; X represents halogen or hydrogen; Y represents nitro or amino which may be protected with a protecting group; and m and n each represents an integer of from 1 to 6; and processes for producing the 2-arylquinolines.
Claims29
2-Arylquinoline represented by the following formula (1):
- ##STR4## wherein R.sup.1, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8 and R.sup.9 each independently represents a hydrogen atom, a halogen atom, a lower alkyl group, a cyclic lower alkyl group, an aryl group, an aralkyl group, an alkoxy group or --C.sub.m F.sub.2m+1 ;
- R.sup.2 represents a hydrogen atom, a halogen atom, a lower alkyl group, a cyclic lower alkyl group, an aryl group, an aralkyl group, an alkoxy group, --C.sub.n F.sub.2n+1 or --CH.sub.2 Q, in which Q represents a monovalent organic group obtained by eliminating from an organic compound having an --NH-- group the hydrogen atom bonded to the nitrogen atom or Q represents a halogen atom;
- X represents a halogen atom;
- Y represents a nitro group, an amino group or an amino group protected with a protecting group;
- and
- m and n each independently represents an integer of from 1 to 6.
2-Arylquinoline represented by the following formula (1):
- ##STR5## wherein R.sup.1, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8 and R.sup.9 each independently represents a hydrogen atom, a halogen atom, a lower alkyl group, a cyclic lower alkyl group, an aryl group, an aralkyl group, an alkoxy group or --C.sub.m F.sub.2m+1 ;
- R.sup.2 represents --CH.sub.2 Q, in which Q represents a monovalent organic group obtained by eliminating from an organic compound having an --NH-- group the hydrogen atom bonded to the nitrogen atom or Q represents a halogen atom;
- X represents a hydrogen atom;
- Y represents a nitro group, an amino group or an amino group protected with a protecting group;
- and
- m represents an integer of from 1 to 6.
2-Arylquinoline represented by the following formula (1):
- ##STR6## wherein R.sup.1, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8 and R.sup.9 each independently represents a hydrogen atom, a halogen atom, a lower alkyl group, a cyclic lower alkyl group, a aryl group, an aralkyl group, an alkoxy group or --C.sub.m F.sub.2m+1 ;
- R.sup.2 represents --CH.sub.2 Q, in which Q represents a 3H-imidazo4,5-b!pyridin-3-yl group which is optionally substituted or Q represents a bromine atom;
- X represents a halogen atom or a hydrogen atom;
- Y represents a nitro group, an amino group or an amino group protected with a protecting group;
- and
- m represents an integer of from 1 to 6.
4-chloro-6-(2-ethyl-5,7-dimethyl-3H-imidazo4,5-b!pyrid in-3-yl)methyl!-2-(2-nitrophenyl)quinoline or 2-{6-(2-ethyl-5,7-dimethyl-3H-imidazo4,5-b!pyridin-3-yl)methyl!quinolin- 2-yl}aniline.
A process for producing a 4-halo-2-(nitrophenyl)quinoline represented by the following formula (1), wherein X represents a halogen atom, and Y represents a nitro group,
- which comprises reacting a 2-(nitrophenyl)-4-quinolone represented by the following formula (2), wherein Y represents a nitro group, with a halogenation agent:
- ##STR7## wherein, in formulae (1) and (2), R.sup.1, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8 and R.sup.9 each independently represents a hydrogen atom, a halogen atom, a lower alkyl group, a cyclic lower alkyl group, an aryl group, an aralkyl group, an alkoxy group or --C.sub.m F.sub.2m+1 ;
- R.sup.2 represents a hydrogen atom, a halogen atom, a lower alkyl group, a cyclic lower alkyl group, an aryl group, an aralkyl group, an alkoxy group, --C.sub.n F.sub.2n+1 or --CH.sub.2 Q, in which Q represents a monovalent organic group obtained by eliminating from an organic compound having an --NH-- group the hydrogen atom bonded to the nitrogen atom, or a halogen atom;
- and
- m and n each independently represents an integer of from 1 to 6.
A process for producing a (quinolin-2-yl)aniline represented by the following formula (1), wherein X represents a hydrogen atom, and Y represents an amino group,
- which comprises reducing 4-halo-2-(nitrophenyl)quinoline represented by formula (1), wherein X represents a halogen atom, and Y represents a nitro group, with a reducing agent in the presence of a base ##STR8## wherein R.sup.1, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8 and R.sup.9 each independently represents a hydrogen atom, a halogen atom, a lower alkyl group, a cyclic lower alkyl group, an aryl group, an aralkyl group, an alkoxy group or --C.sub.m F.sub.2m+1 ;
- R.sup.2 represents a hydrogen atom, a halogen atom, a lower alkyl group, a cyclic lower alkyl group, an aryl group, an aralkyl group, an alkoxy group, --C.sub.n F.sub.2n+1 or --CH.sub.2 Q, in which Q represents a monovalent organic group obtained by eliminating from an organic compound having an --NH-- group the hydrogen atom bonded to the nitrogen atom or Q represents a halogen atom;
- and
- m and n each independently represents an integer of from 1 to 6.
Dependencies are inferred from the claim text.