Regioselective aluminium chloride induced heteroarylation of pyrrolo[1,2-b]pyridazines: Its scope and application

Tetrahedron

Volumn 58, Issue 50, 2002, Pages 9933-9940

  Pal, Manojit ^a   Batchu, Venkateswara Rao ^a   Khanna, Smriti ^a   Yeleswarapu, Koteswar Rao ^a  

^a DR REDDY'S LABORATORIES LTD   (India)

Author keywords

Aluminium chloride; C C bond formation; Pyridazines; Regioselective heteroarylation

Indexed keywords

2 METHYL 3 (1,4,5,6 TETRAHYDRONICOTINOYL)PYRAZOLO[1,5 A]PYRIDINE; 3,6 DICHLOROPYRIDAZINE; 6 (2,4 DIMETHOXYPHENYL) 2 METHYLPYRROLO[1,2 B]PYRIDAZINE; 6 (3 FLUORO 4 METHYLPHENYL) 2 METHYLPYRROLO[1,2 B]PYRIDAZINE; 6 (4 CHLOROPHENYL) 2 METHYLPYRROLO[1,2 B]PYRIDAZINE; 6 (4 FLUOROPHENYL) 2 METHYLPYRROLO[1,2 B]PYRIDAZINE; 6 (4 ISOBUTYLPHENYL) 2 METHYLPYRROLO[1,2 B]PYRIDAZINE; 6 (4 METHOXYPHENYL) 2 METHYLPYRROLO[1,2 B]PYRIDAZINE; 6 (4 METHYLPHENYL) 2 METHYLPYRROLO[1,2 B]PYRIDAZINE; 6 (4 NITROPHENYL) 2 METHYLPYRROLO[1,2 B]PYRIDAZINE; 6 (ETHYLPHENYL) 2 METHYLPYRROLO[1,2 B]PYRIDAZINE; 6 OXO 3 (2 PHENYLPYRAZOLO[1,5 A]PYRIDIN 3 YL) 1(6H) PYRIDAZINEBUTYRIC ACID; 7 (6 CHLORO 3 PYRIDAZINYL) 6 (2,4 DIMETHOXYPHENYL) 2 METHYLPYRROLO[1,2 B]PYRIDAZINE; 7 (6 CHLORO 3 PYRIDAZINYL) 6 (3 FLUORO 4 METHYLPHENYL) 2 METHYLPYRROLO[1,2 B]PYRIDAZINE; 7 (6 CHLORO 3 PYRIDAZINYL) 6 (4 CHLOROPHENYL) 2 METHYLPYRROLO[1,2 B]PYRIDAZINE; 7 (6 CHLORO 3 PYRIDAZINYL) 6 (4 ETHYLPHENYL) 2 METHYLPYRROLO[1,2 B]PYRIDAZINE; 7 (6 CHLORO 3 PYRIDAZINYL) 6 (4 FLUOROPHENYL) 2 METHYLPYRROLO[1,2 B]PYRIDAZINE; 7 (6 CHLORO 3 PYRIDAZINYL) 6 (4 ISOBUTYLPHENYL) 2 METHYLPYRROLO[1,2 B]PYRIDAZINE; 7 (6 CHLORO 3 PYRIDAZINYL) 6 (4 METHOXYPHENYL) 2 METHYLPYRROLO[1,2 B]PYRIDAZINE; 7 (6 CHLORO 3 PYRIDAZINYL) 6 (4 METHYLPHENYL) 2 METHYLPYRROLO[1,2 B]PYRIDAZINE; 7 (6 CHLORO 3 PYRIDAZINYL) 6 (4 NITROPHENYL) 2 METHYLPYRROLO[1,2 B]PYRIDAZINE; 7 (6 METHOXY 3 PYRIDAZINYL) 2 METHYL 6 (4 METHYLPHENYL)PYRROLO[1,2 B]PYRIDAZINE; ALUMINUM CHLORIDE; AZOLOPYRIDAZINE; PYRIDAZINE DERIVATIVE; PYRROLO[1,2 B]PYRIDAZINE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CHEMICAL BOND; DRUG SYNTHESIS; PRIORITY JOURNAL; SUBSTITUTION REACTION;

EID: 0037049283     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01352-2     Document Type: Article

References (48)

1. (a) Tisler M., Stanovnik B. Katritzky A.R., Heterocyclic Chemistry. Vol. 49:1990;1 Academic, San Diego.
2. (a) Tisler M., Stanovnik B. Katritzky A.R., Heterocyclic Chemistry. Vol. 49:1990;1 Academic, San Diego, (b) Coates W.J., McKillop A. Synthesis. 3:1993;334.
3. (a) Heinisch G., Kopelent H. Ellis G.P., West G.B., Progress in Medicinal Chemistry. Vol. 29:1992;141 Elsevier, Amsterdam.
4. (b) Ungureanu M., Mangalagiu I., Grosu G., Petrovanu M. Ann. Pharm. Fr. 55:1997;2-69.
5. For biological activities of 6-heteroaryl substituted-3-pyridazinone derivatives see; (c) Gokçe M., Dogruer D., Sahin M.F. IL Farmaco. 56:2001;233 (d) Jonas R., Klockow M., Lues I., Pruecher H., Schliep H.J., Wurziger H., Eur. J. Med. Chem. Chim. Ther. 28:1993;129 (e) McEvoy F.J., Allen G.R. Jr. J. Med. Chem. 17:1974;281.
6. For biological activities of 6-heteroaryl substituted-3-pyridazinone derivatives see; (c) Gokçe M., Dogruer D., Sahin M.F. IL Farmaco. 56:2001;233 (d) Jonas R., Klockow M., Lues I., Pruecher H., Schliep H.J., Wurziger H., Eur. J. Med. Chem. Chim. Ther. 28:1993;129 (e) McEvoy F.J., Allen G.R. Jr. J. Med. Chem. 17:1974;281.
7. (a) Heinisch G., Kopelent H. Ellis G.P., West G.B., Progress in Medicinal Chemistry. Vol. 29:1992;141 Elsevier, Amsterdam, (b) Ungureanu M., Mangalagiu I., Grosu G., Petrovanu M. Ann. Pharm. Fr. 55:1997;2-69. For biological activities of 6-heteroaryl substituted-3-pyridazinone derivatives see; (c) Gokçe M., Dogruer D., Sahin M.F. IL Farmaco. 56:2001;233 (d) Jonas R., Klockow M., Lues I., Pruecher H., Schliep H.J., Wurziger H., Eur. J. Med. Chem. Chim. Ther. 28:1993;129 (e) McEvoy F.J., Allen G.R. Jr. J. Med. Chem. 17:1974;281.
8. Deeb A., Said S.A. Collect. Czech. Chem. Commun. 55:1990;2795.
9. Akahane A., Katayama H., Mitsunaga T., Kato T., Kinoshita T., Kita Y., Kusunoki T., Terai T., Yoshida K., Shiokawa Y. J. Med. Chem. 42:1999;779.
10. Kuroda S., Akahane A., Itani H., Nishimura S., Durkin K., Kinoshita T., Tenda Y., Sakane K. Bioorg. Med. Chem. Lett. 9:1999;1979.
11. Beswick, P.; Campbell, I.; Naylor, A. World Patent WO9912930-A1; Chem Abstr. 1999, 130, 223286.
12. Almansa C., de Arriba A.F., Cavalcanti F.L., Gómez L.A., Miralles A., Merlos M., García-Rafanell J., Forn J. J. Med. Chem. 44:2001;350.
13. Nakashima M., Kanamaru M., Uematsu T., Nagashima S., Mizuno A., Toriumi C., Hotta M., Komuro M., Ishida R., Uchida H. Eur. J. Pharmacol. 2:1990;183. Abst P.mo.375.
14. (a) Nasir, A. I.; Gundersen, L.-L.; Rise F.; Antonsen, Ø Kristensen, T.; Langhelle, B.; Bast, A.; Custers, I.; Haenen G. R. M. M.; Wikström, H. Bioorg. Med. Chem. Lett. 1998, 8, 1829.
15. (b) Matsuo, M.; Manabe, T.; Okumura, H.; Matsuda, H.; Fujii, N. World Patent WO 9118903 A1, 12 December 1991; Chem. Abstr. 1992, 130, 151782.
16. (c) Ohtani, M.; Fuji, M.; Fukui, Y.; Adachi, M. World Patent WO 9959999 A1, 25 November 1999; Chem. Abstr. 2000, 132, 12318.
17. (d) Ungureanu, M.; Mangalagiu, I.; Grosu, G.; Petrovanu, M. Ann. Pharm. Fr. 1997, 55 (2), 69. Chem. Abstr. 1997, 126, 303587
18. (a) Pal, M.; Rao, Y. K.; Rajagopalan, R.; Misra, P.; Kumar, P. M.; Rao, C. S. World Patent WO 01/90097, 29 November 2001; Chem. Abstr. 2002, 136, 5893. (b) Pattabiraman, V.R.; Padakanti, P.S.; Veeramaneni, V.R.; Pal, M.; Yeleswarapu, K.R. Synlett 2002, 947. For a brief overview see: (c) Scrip 2002, 112, 43.
19. (a) Pal, M.; Rao, Y. K.; Rajagopalan, R.; Misra, P.; Kumar, P. M.; Rao, C. S. World Patent WO 01/90097, 29 November 2001; Chem. Abstr. 2002, 136, 5893. (b) Pattabiraman, V.R.; Padakanti, P.S.; Veeramaneni, V.R.; Pal, M.; Yeleswarapu, K.R. Synlett 2002, 947. For a brief overview see: (c) Scrip 2002, 112, 43.
20. (a) Pal, M.; Rao, Y. K.; Rajagopalan, R.; Misra, P.; Kumar, P. M.; Rao, C. S. World Patent WO 01/90097, 29 November 2001; Chem. Abstr. 2002, 136, 5893. (b) Pattabiraman, V.R.; Padakanti, P.S.; Veeramaneni, V.R.; Pal, M.; Yeleswarapu, K.R. Synlett 2002, 947. For a brief overview see: (c) Scrip 2002, 112, 43.
21. Fraser M. J. Org. Chem. 36:1971;3087.
22. (a) Weidner C.H., Michaels F.M., Beltman D.J., Montgomery C.J., Wadsworth D.H., Briggs B.T., Picone M.L. J. Org. Chem. 56:1991;5594
23. (b) Lown J.W., Matsumoto K. Can. J. Chem. 49:1971;1165.
24. (a) Kobayashi Y., Kutsuma T., Morinaga K. Chem. Pharm. Bull. 19:1971;2106
25. (b) Masaki Y., Otsuka H., Nakayama Y., Hioki M. Chem. Pharm. Bull. 21:1973;2780
26. (c) Sasaki T., Kanematsu K., Yukimoto Y., Ochiai S. J. Org. Chem. 36:1971;813.
27. (a) Kundu N.G., Pal M. J. Chem. Soc., Chem. Commun. 1993;86
28. (b) Kundu N.G., Pal M., Mahanty J.S., De M. J. Chem. Soc., Perkin Trans. 1. 1997;2815
29. (c) Roesch K.R., Larock R.C. Org. Lett. 1:1999;1551
30. (d) Østby O.B., Dalhus B., Gundersen L.-L., Rise F., Bast A., Haenen G.R.M.M. Eur. J. Org. Chem. 2000;3763.
31. (e) For an excellent review see: Undheim K., Benneche T. Adv. Heterocycl. Chem. 62:1995;304
32. (f) Maes B.U.W., Kosmrlj J., Lemiere G.L.F. J. Heterocycl. Chem. 39:2002;535. and references cited therein.
33. (a) Coates W.J., McKillop A. J. Org. Chem. 55:1990;5418.
34. (a) Coates W.J., McKillop A. J. Org. Chem. 55:1990;5418 (b) Berkes D., Kovac J. Collect. Czech. Chem. Commun. 51:1986;1450.
35. Vysotskii Y.B., Zemskii B.P. Khim. Geterotsikl. Soedin. 984:1980;. Chem. Abstr. 1980, 93, 238535.
36. Matsumoto K., Uchida T., Ikemi Y., Tanaka T., Asahi M., Kato T., Konishi H. Bull. Chem. Soc. Jpn. 60:1987;3645.
37. Overberger C., Byrd N., Mesrobian R. J. Am. Chem. Soc. 78:1956;1961.
38. (a) Buess, C. M.; Brandt, V. O.; Srivastava, R. C.; Carper, W. R. J. Heterocycl. Chem. 1972, 9, 887. (b) Kulkarni, Y. D.; Saxena, N.; Srivastava, O. P. Indian J. Chem. Sect. A 1990, 29, 77. (c) Radchenko, O. S.; Novikov, V. L.; Willis, R. H.; Murphy, P. T.; Elyakov, G. B. Tetrahedron Lett. 1997, 38, 3581. (d) Rival, Y.; Grassy, G.; Michel, G. Chem. Pharm. Bull. 1992, 40, 1170. For the preparation of N-[4-(2-bromoacetyl)-phenyl]methanesulfonamide see: (e) Zanka, A.; Kubota, A.; Hirabayashi, S.; Nukamura, H. Org. Process. Res. Dev. 1998, 2, 71. For the preparation of 4-isobutylacetophenone see: (f) Lindley, C. R.; Eur. Pat. Appl. EP 488638 A1, 3 June 1992; Chem. Abstr. 117:111254.
39. (a) Buess, C. M.; Brandt, V. O.; Srivastava, R. C.; Carper, W. R. J. Heterocycl. Chem. 1972, 9, 887. (b) Kulkarni, Y. D.; Saxena, N.; Srivastava, O. P. Indian J. Chem. Sect. A 1990, 29, 77. (c) Radchenko, O. S.; Novikov, V. L.; Willis, R. H.; Murphy, P. T.; Elyakov, G. B. Tetrahedron Lett. 1997, 38, 3581. (d) Rival, Y.; Grassy, G.; Michel, G. Chem. Pharm. Bull. 1992, 40, 1170. For the preparation of N-[4-(2-bromoacetyl)-phenyl]methanesulfonamide see: (e) Zanka, A.; Kubota, A.; Hirabayashi, S.; Nukamura, H. Org. Process. Res. Dev. 1998, 2, 71. For the preparation of 4-isobutylacetophenone see: (f) Lindley, C. R.; Eur. Pat. Appl. EP 488638 A1, 3 June 1992; Chem. Abstr. 117:111254.
40. (a) Buess, C. M.; Brandt, V. O.; Srivastava, R. C.; Carper, W. R. J. Heterocycl. Chem. 1972, 9, 887. (b) Kulkarni, Y. D.; Saxena, N.; Srivastava, O. P. Indian J. Chem. Sect. A 1990, 29, 77. (c) Radchenko, O. S.; Novikov, V. L.; Willis, R. H.; Murphy, P. T.; Elyakov, G. B. Tetrahedron Lett. 1997, 38, 3581. (d) Rival, Y.; Grassy, G.; Michel, G. Chem. Pharm. Bull. 1992, 40, 1170. For the preparation of N-[4-(2-bromoacetyl)-phenyl]methanesulfonamide see: (e) Zanka, A.; Kubota, A.; Hirabayashi, S.; Nukamura, H. Org. Process. Res. Dev. 1998, 2, 71. For the preparation of 4-isobutylacetophenone see: (f) Lindley, C. R.; Eur. Pat. Appl. EP 488638 A1, 3 June 1992; Chem. Abstr. 117:111254.
41. (a) Buess, C. M.; Brandt, V. O.; Srivastava, R. C.; Carper, W. R. J. Heterocycl. Chem. 1972, 9, 887. (b) Kulkarni, Y. D.; Saxena, N.; Srivastava, O. P. Indian J. Chem. Sect. A 1990, 29, 77. (c) Radchenko, O. S.; Novikov, V. L.; Willis, R. H.; Murphy, P. T.; Elyakov, G. B. Tetrahedron Lett. 1997, 38, 3581. (d) Rival, Y.; Grassy, G.; Michel, G. Chem. Pharm. Bull. 1992, 40, 1170. For the preparation of N-[4-(2-bromoacetyl)-phenyl]methanesulfonamide see: (e) Zanka, A.; Kubota, A.; Hirabayashi, S.; Nukamura, H. Org. Process. Res. Dev. 1998, 2, 71. For the preparation of 4-isobutylacetophenone see: (f) Lindley, C. R.; Eur. Pat. Appl. EP 488638 A1, 3 June 1992; Chem. Abstr. 117:111254.
42. (a) Buess, C. M.; Brandt, V. O.; Srivastava, R. C.; Carper, W. R. J. Heterocycl. Chem. 1972, 9, 887. (b) Kulkarni, Y. D.; Saxena, N.; Srivastava, O. P. Indian J. Chem. Sect. A 1990, 29, 77. (c) Radchenko, O. S.; Novikov, V. L.; Willis, R. H.; Murphy, P. T.; Elyakov, G. B. Tetrahedron Lett. 1997, 38, 3581. (d) Rival, Y.; Grassy, G.; Michel, G. Chem. Pharm. Bull. 1992, 40, 1170. For the preparation of N-[4-(2-bromoacetyl)-phenyl]methanesulfonamide see: (e) Zanka, A.; Kubota, A.; Hirabayashi, S.; Nukamura, H. Org. Process. Res. Dev. 1998, 2, 71. For the preparation of 4-isobutylacetophenone see: (f) Lindley, C. R.; Eur. Pat. Appl. EP 488638 A1, 3 June 1992; Chem. Abstr. 117:111254.
43. For the preparation of N-[4-(2-bromoacetyl)-phenyl]methanesulfonamide see: (e) Zanka, A.; Kubota, A.; Hirabayashi, S.; Nukamura, H. Org. Process. Res. Dev. 1998, 2, 71. For the preparation of 4-isobutylacetophenone see: (f) Lindley, C. R.; Eur. Pat. Appl. EP 488638 A1, 3 June 1992; Chem. Abstr. 117:111254.
44. (a) Buess, C. M.; Brandt, V. O.; Srivastava, R. C.; Carper, W. R. J. Heterocycl. Chem. 1972, 9, 887. (b) Kulkarni, Y. D.; Saxena, N.; Srivastava, O. P. Indian J. Chem. Sect. A 1990, 29, 77. (c) Radchenko, O. S.; Novikov, V. L.; Willis, R. H.; Murphy, P. T.; Elyakov, G. B. Tetrahedron Lett. 1997, 38, 3581. (d) Rival, Y.; Grassy, G.; Michel, G. Chem. Pharm. Bull. 1992, 40, 1170. For the preparation of N-[4-(2-bromoacetyl)-phenyl]methanesulfonamide see: (e) Zanka, A.; Kubota, A.; Hirabayashi, S.; Nukamura, H. Org. Process. Res. Dev. 1998, 2, 71. For the preparation of 4-isobutylacetophenone see: (f) Lindley, C. R.; Eur. Pat. Appl. EP 488638 A1, 3 June 1992; Chem. Abstr. 117:111254.
45. (a) Scriven E.F.V. Katritzky A.R., Ress C.W., Comprehensive Heterocyclic Chemistry. Vol. 2:1984;165 Pergamon, Oxford.
46. (a) Scriven E.F.V. Katritzky A.R., Ress C.W., Comprehensive Heterocyclic Chemistry. Vol. 2:1984;165 Pergamon, Oxford, (b) Abramovitch R.A., Saha J.G. Adv. Heterocycl. Chem. 6:1966;229.
47. Pearson D.E., Hargrove W.W., Chow J.K.T., Suthers B.R. J. Org. Chem. 26:1961;789.
48. Parrot I., Rival Y., Wermuth C.G. Synthesis. 7:1999;1163.