PROCESS FOR PREPARING HALOGENATED IMIDAZOPYRIDINE DERIVATIVESThe present invention relates to a process for preparing halogenated imidazopyridine derivatives of the formula (II) starting from compounds of the formula (I) via intermediates of the formula (IVa) or (IVb) in which the radicals Q, Z, R1, R3, R4, Rc, A1 and A2 have the abovementioned meanings. The invention furthermore relates to such halogenated imidazopyridine derivatives and to intermediates and reaction products from compounds of the formula (II) to give compounds of the formula (III) in which the above structural units have the abovementioned meanings.The method for preparing the compound of formula (ii)whereinq and z independently are halogen,a1for nitrogen ,=n+-o-or=c-r5,a2for-n-r6, oxygen or sulphur,r1for (c1-c6) alkyl, (c1-c6) halogenated alkyl, (c1-c6) cyanoalkyl, (c1-c6) hydroxy alkyl, (c1-c6) alcoxyl base-(c1-c6) alkyl, (c1-c6) halogenated alkoxy-(c1-c6) alkyl, (c2-c6) alkenyl, (c2-c6) alkenyloxy group-(c1-c6) alkane base, (c2-c6) haloalkenyloxy-(c1-c6) alkyl, (c2-c6) halogenated alkenyl, (c2-c6) cyano alkenyl, (c2-c6) alkynyl, (c2- c6) alkynyloxy group-(c1-c6) alkyl, (c2-c6) halogenated alkynyloxy group-(c1-c6) alkyl, (c2-c6) halo alkynyl, (c2-c6) cyano alkynes base, (c3-c8) naphthenic base, (c3-c6) halogenated cycloalkyl, (c3-c6) cyanocycloalkyl, (c3-c8) naphthenic base-(c3-c8) cycloalkanes base, (c1-c6) alkyl-(c3-c8) naphthenic base, halogenated (c3-c8) naphthenic base, amino, (c1-c6) alkyl amino, two (c1-c6) alkane base amino, (c3-c8) cycloalkyl amino, (c1-c6) alkyl-carbonyl-amino, (c1-c6) alkylthio group-(c1-c6) alkyl, (c1-c6) halogen for alkylthio group-(c1-c6) alkyl, (c1-c6) alkyl sulphinyl-(c1-c6) alkyl, (c1-c6) alkylsulfinyl- (c1-c6) alkyl, (c1-c6) alkyl sulphonyl-(c1-c6) alkyl, (c1-c6) halogenated alkyl sulfonyl-(c1-c6) alkyl, (c1- c6) alkoxy-(c1-c6) alkylthio group-(c1-c6) alkyl, (c1-c6) alkoxy-(c1-c6) alkyl sulphinyl-(c1-c6) alkane base, (c1-c6) alkoxy-(c1-c6) alkyl sulphonyl-(c1-c6) alkyl, (c1-c6) alkyl-carbonyl-(c1-c6) alkyl, (c1- c6) halogenated alkyl carbonyl-(c1-c6) alkyl, (c1-c6) alkoxy carbonyl-(c1-c6) alkyl, (c1-c6) halo alkoxy carbonyl- (c1-c6) alkyl, (c1-c6) alkyl sulfonyl-amino, amino-sulfonyl-(c1-c6) alkyl, (c1-c6) alkyl amino sulfonyl- (c1-c6) alkyl, two (c1-c6) alkyl amino sulfonyl-(c1-c6) alkyl,it or is (c1-c6) alkyl, (c1-c6) alkoxy, (c2-c6) alkenyl, (c2-c6) alkynyl, (c3-c8) naphthenic base, respectively appoint selection of land is monosubstituted or polysubstituted by identical or different substituent group, and the substituent group is selected from aryl, heteroaryl and heterocycle, wherein aryl, heteroaryl and heterocycle can be respectively optionally monosubstituted or polysubstituted by identical or different substituent group selected from the following: halogen, cyano, nitro, hydroxyl, amino, carboxyl, carbamoyl, amino-sulfonyl, (c1-c6) alkyl, (c3-c6) naphthenic base, (c1-c6) alkoxy, (c1-c6) halogenated alkyl, (c1-c6) halogenated alkoxy, (c1-c6) alkylthio group, (c1-c6) alkyl sulfenyl base, (c1-c6) alkyl sulphonyl, (c1-c6) alkyl sulfenyl imino group, (c1-c6) alkyl sulfenyl imino group-(c1-c6) alkane base, (c1-c6) alkyl sulfenyl imino group-(c2-c6) alkyl-carbonyl, (c1-c6) alkyl sulfonyl imino group, (c1-c6) alkyl sulfonyl imino group-(c1-c6) alkyl, (c1-c6) alkyl sulfonyl imino group-(c2-c6) alkyl-carbonyl, (c1-c6) alkoxy carbonyl, (c1- c6) alkyl-carbonyl, (c3-c6) trialkylsilkl and benzyl,r3for hydrogen, cyano, halogen, nitro, acetyl group, hydroxyl, amino, scn, three (c1-c6) aikylsilyl groups, (c3-c8) ring alkyl, (c3-c8) naphthenic base-(c3-c8) naphthenic base, (c1-c6) alkyl-(c3-c8) naphthenic base, halogenated (c3-c8) naphthenic base, cyanogen base (c3-c8) naphthenic base, (c1-c6) alkyl, (c1-c6) halogenated alkyl, (c1-c6) cyanoalkyl, (c1-c6) hydroxy alkyl, hydroxyl carbonyl-(c1-c6)-alkoxy, (c1-c6) alkoxy carbonyl-(c1-c6) alkyl, (c1-c6) alkoxy-(c1-c6) alkyl, (c2- c6) alkenyl, (c2-c6) halogenated alkenyl, (c2-c6) cyano alkenyl, (c2-c6) alkynyl, (c2-c6) halo alkynyl, (c2-c6) cyano alkynes base, (c1-c6) alkoxy, (c1-c6) halogenated alkoxy, (c1-c6) cyano alkoxy, (c1-c6) alkoxy carbonyl-(c1-c6) alkane oxygroup, (c1-c6) alkoxy-(c1-c6) alkoxy, (c1-c6) alkyl hydroxy imino group, (c1-c6) alkoximino, (c1- c6) alkyl-(c1-c6) alkoximino, (c1-c6) halogenated alkyl-(c1-c6) alkoximino, (c1-c6) alkylthio group, (c1-c6) halogenated alkylthio, (c1-c6) alkoxy-(c1-c6) alkylthio group, (c1-c6) alkylthio group-(c1-c6) alkyl, (c1-c6) alkane base sulfinyl, (c1-c6) alkylsulfinyl, (c1-c6) alkoxy-(c1-c6) alkyl sulphinyl, (c1-c6) alkyl sulfinyl-(c1-c6) alkyl, (c1-c6) alkyl sulphonyl, (c1-c6) halogenated alkyl sulfonyl, (c1-c6) alkoxy-(c1- c6) alkyl sulphonyl, (c1-c6) alkyl sulphonyl-(c1-c6) alkyl, (c1-c6) alkyl sulphonyl oxygroup, (c1-c6) alkyl oxycarbonyl base, (c1-c6) alkyl thiocarbonyl, (c1-c6) halogenated alkyl carbonyl, (c1-c6) alkyl carbonyl epoxide, (c1-c6) alkoxy carbonyl base, (c1-c6) halo alkoxy carbonyl, amino carbonyl, (c1-c6) alkyl amino-carbonyl, (c1-c6) thio-alkyl amino-carbonyl, two (c1-c6) alkyl amino-carbonyl, two (c1-c6) thio-alkyl amino-carbonyl, (c2-c6) alkenyl amino carbonyl, two (c2-c6) alkene base amino carbonyl, (c3-c8) cycloalkyl amino carbonyl, (c1-c6) alkyl sulfonyl-amino, (c1-c6) alkyl amino, two (c1-c6) alkyl amino, amino-sulfonyl, (c1-c6) alkyl amino sulfonyl, two (c1-c6) alkyl amino sulfonyl, (c1-c6) alkyl sulphur acylimino, aminothiocarbonyl, (c1-c6) thio-alkyl amino-carbonyl, two (c1-c6) thio-alkyl amino-carbonyl, (c3-c8) cycloalkyl amino ,-nhco- (c1-c6) alkyl ((c1-c6) alkyl-carbonyl-amino), orit is respe...
할로겐화 이미다조피리딘 유도체의 제조 방법 본 발명은 화학식 (I)의 화합물로부터 출발하여 (IVa) 또는 (IVb)의 중간체를 거쳐 화학식 (II)의 할로겐화 이미다조피리딘 유도체를 제조하는 방법에 관한 것이다:[이미지][이미지][이미지] 상기 식들에서, Q, Z, R1, R3, R4, Rc, A1 및 A2는 명세서에 주어진 정의를 갖는다. 본 발명은 또한 상기 할로겐화 이미다조피리딘 유도체, 및 화학식 (III)의 화합물을 제공하기 위한 중간체 및 화학식 (II)의 화합물의 반응 생성물에 관한 것이다:[이미지] 상기 식에서 나타낸 구조 요소들은 명세서에 주어진 정의를 갖는다.제1 방법 단계 a)에서, 화학식 (I)의 화합물을 구조 (NRaRb)-Zn-Rc 또는 (NRaRb)2-Zn (여기서, Rc는 할로겐 또는 -O-피발로일이고, Ra 및 Rb는 함께, 각각 1, 2, 3 또는 4개의 Rd 라디칼에 의해 임의로 치환될 수 있는 -(CH2)4-, -(CH2)5- 또는 -(CH2)2O(CH2)2- 그룹을 형성하고, 여기서 Rd는 메틸, 에틸, n-프로필 및 이소프로필로 구성된 그룹으로부터 선택됨)의 유기 아연 염기와 반응시켜 화학식 (IVa) 또는 화학식 (IVb)의 화합물을 제공하고,제2 방법 단계 b)에서 상기 화학식 (IVa) 또는 (IVb)의 화합물을 구조 Q-V의 화합물 (여기서, V는 할로겐이고, Q는 아래에 정의된 의미를 가짐)과 반응시켜 화학식 (II)의 화합물을 제공하는 단계를 특징으로 하는,화학식 (II)의 화합물의 제조 방법:[이미지][이미지][이미지]상기 식에서,Q 및 Z는 각각 독립적으로 할로겐이고, A1은 질소, =N+O- 또는 =C-R5이고,A2는 -N-R6, 산소 또는 황이고,R1은 (C1-C6)알킬, (C1-C6)할로알킬, (C1-C6)시아노알킬, (C1-C6)하이드록시알킬, (C1-C6)알콕시-(C1-C6)알킬, (C1-C6)할로알콕시-(C1-C6)알킬, (C2-C6)알케닐, (C2-C6)알케닐옥시-(C1-C6)알킬, (C2-C6)할로알케닐옥시-(C1-C6)알킬, (C2-C6)할로알케닐, (C2-C6)시아노알케닐, (C2-C6)알키닐, (C2-C6)알키닐옥시-(C1-C6)알킬, (C2-C6)할로알키닐옥시-(C1-C6)알킬, (C2-C6)할로알키닐, (C2-C6)시아노알키닐, (C3-C8)사이클로알킬, (C3-C6)할로사이클로알킬, (C3-C6)시아노사이클로알킬, (C3-C8)사이클로알킬-(C3-C8)사이클로알킬, (C1-C6)알킬-(C3-C8)사이클로알킬, 할로(C3-C8)사이클로알킬, 아미노, (C1-C6)알킬아미노, 디(C1-C6)알킬아미노, (C3-C8)사이클로알킬아미노, (C1-C6)알킬카보닐아미노, (C1-C6)알킬티오-(C1-C6)알킬, (C1-C6)할로알킬티오-(C1-C6)알킬, (C1-C6)알킬설피닐-(C1-C6)알킬, (C1-C6)할로알킬설피닐-(C1-C6)알킬, (C1-C6)알킬설포닐-(C1-C6)알킬, (C1-C6)할로알킬설포닐-(C1-C6)알킬, (C1-C6)알콕시-(C1-C6)알킬티오-(C1-C6)알킬, (C1-C6)알콕시-(C1-C6)알킬설피닐-(C1-C6)알킬, (C1-C6)알콕시-(C1-C6)알킬설포닐-(C1-C6)알킬, (C1-C6)알킬카보닐-(C1-C6)알킬, (C1-C6)할로알킬카보닐-(C1-C6)알킬, (C1-C6)알콕시카보닐-(C1-C6)알킬, (C1-C6)할로알콕시카보닐-(C1-C6)알킬, (C1-C6)알킬설포닐아미노, 아미노설포닐-(C1-C6)알킬, (C1-C6)알킬아미노설포닐-(C1-C6)알킬, 디(C1-C6)알킬아미노설포닐-(C1-C6)알킬이거나, 또는각각 아릴, 헤트아릴 및 헤테로사이클릴로 구성된 그룹으로부터의 동일하거나 상이한 치환체에 의해 임의로 일- 또는 다치환된 (C1-C6)알킬, (C1-C6)알콕시, (C2-C6)알케닐, (C2-C6)알키닐, (C3-C8)사이클로알킬이고, 여기서 아릴, 헤트아릴 또는 헤테로사이클릴은 각각 할로겐, 시아노, 니트로, 하이드록실, 아미노, 카복시, 카바모일, 아미노설포닐, (C1-C6)알킬, (C3-C6)사이클로알킬, (C1-C6)알콕시, (C1-C6)할로알킬, (C1-C6)할로알콕시, (C1-C6)알킬티오, (C1-C6)알킬설피닐, (C1-C6)알킬설포닐, (C1-C6)알킬설프이미노, (C1-C6)알킬설프이미노-(C1-C6)알킬, (C1-C6)알킬설프이미노-(C2-C6)알킬카보닐, (C1-C6)알킬설폭스이미노, (C1-C6)알킬설폭스이미노-(C1-C6)알킬, (C1-C6)알킬설폭스이미노-(C2-C6)알킬카보닐, (C1-C6)알콕시카보닐, (C1-C6)알킬카보닐, (C3-C6)트리알킬실릴 및 벤질로 구성된 그룹으로부터의 동일하거나 상이한 치환체에 의해 임의로 일- 또는 다치환될 수 있고,R3은 수소,시아노, 할로겐, 니트로, 아세틸, 하이드록실, 아미노, SCN, 트리(C1-C6)알킬실릴, (C3-C8)사이클로알킬, (C3-C8)사이클로알킬-(C3-C8)사이클로알킬, (C1-C6)알킬-(C3-C8)사이클로알킬, 할로(C3-C8)사이클로알킬, 시아노(C3-C8)사이클로알킬, (C1-C6)알킬, (C1-C6)할로알킬, (C1-C6)시아노알킬, (C1-C6)하이드록시알킬, 하이드록시카보닐-(C1-C6)-알콕시, (C1-C6)알콕시카보닐-(C1-C6)알킬, (C1-C6)알콕시-(C1-C6)알킬, (C2-C6)알케닐, (C2-C6)할로알케닐, (C2-C6)시아노알케닐, (C2-C6)알키닐, (C2-C6)할로알키닐, (C2-C6)시아노알키닐, (C1-C6)알콕시, (C1-C6)할로알콕시, (C1-C6)시아노알콕시, (C1-C6)알콕시카보닐-(C1-C6)알콕시, (C1-C6)알콕시-(C1-C6)알콕시, (C1-C6)알킬하이드록시이미노, (C1-C6)알콕시이미노, (C1-C6)알킬-(C1-C6)알콕시이미노, (C1-C6)할로알킬-(C1-C6)알콕시이미노, (C1-C6)알킬티오, (C1-C6)할로알킬티오, (C1-C6)알콕시-(C1-C6)알킬티오, (C1-C6)알킬티오-(C1-C6)알킬, (C1-C6)알킬설피닐, (C1-C6)할로알킬설피닐, (C1-C6)알콕시-(C1-C6)알킬설피닐, (C1-C6)알킬설피닐-(C1-C6)알킬, (C1-C6)알킬설포닐, (C1-C6)할로알킬설포닐, (C1-C6)알콕시-(C1-C6)알킬설포닐, (C1-C6)알킬설포닐-(C1-C6)알킬, (C1-C6)알킬설포닐옥시, (C1-C6)알킬카보닐, (C1-C6)알킬티오카보닐, (C1-C6)할로알킬카보닐, (C1-C6)알킬카보닐옥시, (C1-C6)알콕시카보닐, (C1-C6)할로알콕시카보닐, 아미노카보닐, (C1-C6)알킬아미노카보닐, (C1-C6)알킬아미노티오카보닐, 디(C1-C6)알킬아미노카보닐, 디(C1-C6)알킬아미노티오카보닐, (C2-C6)알케닐아미노카보닐, 디(C2-C6)-알케닐아미노카보닐, (C3-C8)사이클로알킬아미노카보닐, (C1-C6)알킬설포닐아미노, (C1-C6)알킬아미노, 디(C1-C6)알킬아미노, 아미노설포닐, (C1-C6)알킬아미노설포닐, 디(C1-C6)알킬아미노설포닐, (C1-C6)알킬설폭스이미노, 아미노티오카보닐, (C1-C6)알킬아미노티오카보닐, 디(C1-C6)알킬아미노티오카보닐, (C3-C8)사이클로알킬아미노, -NHCO-(C1-C6)알킬 ((C1-C6)알킬카보닐아미노)이거나, 또는각각 동일하거나 상이한 치환체에 의해 임의로 일- 또는 다치환된 아릴 또는 헤트아릴이고, 여기서 (헤트아릴의 경우) 적어도 하나의 카보닐 그룹이 임의로 존재할 수 있고 가능한 치환체는 각 경우 다음과 같고: 시아노, 카복실, 할로겐, 니트로, 아세틸, 하이드록실, 아미노, SCN, 트리(C1-C6)알킬실릴, (C1-C6)알킬, (C1-C6)할로알킬, (C1-C6)시아노알킬, (C1-C6)하이드록시알킬, 하이드록시카보닐-(C1-C6)-알콕시, (C1-C6)알콕시카보닐-(C1-C6)알킬, (C1-C6)알콕시-(C1-C6)알킬, (C2-C6)알케닐, (C2-C6)할로알케닐, (C2-C6)시아노알케닐, (C2-C6)알키닐, (C2-C6)할로알키닐, (C2-C6)시아노알키닐, (C1-C6)알콕시, (C1-C6)할로알콕시, (C1-C6)시아노알콕시, (C1-C6)알콕시카보닐-(C1-C6)알콕시, (C1-C6)알콕시-(C1-C6)알콕시, (C1-C6)알킬하이드록시이미노, (C1-C6)알콕시이미노, (C1-C6)알킬-(C1-C6)알콕시이미노, (C1-C6)할로알킬-(C1-C6)알콕시이미노, (C1-C6)알킬티오, (C1-C6)할로알킬티오, (C1-C6)알콕시-(C1-C6)알킬티오, (C1-C6)알킬티오-(C1-C6)알킬, (C1-C6)알킬설피닐, (C1-C6)할로알킬설피닐, (C1-C6)알콕시-(C1-C6)알킬설피닐, (C1-C6)알킬설피닐-(C1-C6)-알킬, (C1-C6)알킬설포닐, (C1-C6)할로알킬설포닐, (C1-C6)알콕시-(C1-C6)알킬설포닐, (C1-C6)알킬설포닐-(C1-C6)알킬, (C1-C6)알킬설포닐옥시, (C1-C6)알킬카보닐, (C1-C6)할로알킬카보닐, (C1-C6)알킬카보닐옥시, (C1-C6)알콕시카보닐, (C1-C6)할로알콕시카보닐, 아미노카보닐, (C1-C6)알킬아미노카보닐, 디(C1-C6)알킬아미노카보닐, (C2-C6)알케닐아미노카보닐, 디(C2-C6)알케닐아미노카보닐, (C3-C8)사이클로알킬아미노카보닐, (C1-C6)알킬설포닐아미노, (C1-C6)알킬아미노, 디(C1-C6)알킬아미노, 아미노설포닐, (C1-C6)알킬아미노설포닐, 디(C1-C6)알킬아미노설포닐, (C1-C6)알킬설폭스이미노, 아미노티오카보닐, (C1-C6)알킬아미노티오카보닐, 디(C1-C6)알킬아미노티오카보닐 또는 (C3-C8)사이클로알킬아미노,R4는 수소,시아노, 할로겐, 니트로, 아세틸, 하이드록실, 아미노, SCN, 트리(C1-C6)알킬실릴, (C3-C8)사이클로알킬, (C3-C8)사이클로알킬-(C3-C8)사이클로알킬, (C1-C6)알킬-(C3-C8)사이클로알킬, 할로(C3-C8)사이클로알킬, 시아노(C3-C8)사이클로알킬, (C1-C6)알킬, (C1-C6)할로알킬, (C1-C6)시아노알킬, (C1-C6)하이드록시알킬, 하이드록시카보닐-(C1-C6)-알콕시, (C1-C6)알콕시카보닐-(C1-C6)알킬, (C1-C6)알콕시-(C1-C6)알킬, (C2-C6)알케닐, (C2-C6)할로알케닐, (C2-C6)시아노알케닐, (C2-C6)알키닐, (C2-C6)할로알키닐, (C2-C6)시아노알키닐, (C1-C6)알콕시, (C1-C6)할로알콕시, (C1-C6)시아노알콕시, (C1-C6)알콕시카보닐-(C1-C6)알콕시, (C1-C6)알콕시-(C1-C6)알콕시, (C1-C6)알킬하이드록시이미노, (C1-C6)알콕시이미노, (C1-C6)알킬-(C1-C6)알콕시이미노, (C1-C6)할로알킬-(C1-C6)알콕시이미노, (C1-C6)알킬티오, (C1-C6)할로알킬티오, (C1-C6)알콕시-(C1-C6)알킬티...