Synthesis of 4-aryl-5-hydroxy- and 5-aryl-4-hydroxypyridazin-3(2H)-ones and their use in the preparation of 4,5-diarylpyridazin-3(2H)-ones and hitherto unknown isochromeno[3,4-d]pyridazinediones

Tetrahedron

Volumn 58, Issue 48, 2002, Pages 9713-9721

  Maes, Bert U W ^a   Monsieurs, Katrien ^a   Loones, Kristof T J ^a   Lemière, Guy L F ^a   Dommisse, Roger ^a   Mátyus, Péter ^b   Riedl, Zsuzsanna ^c   Hajós, György ^c  

^a UNIVERSITY OF ANTWERP   (Belgium)

^b SEMMELWEIS UNIVERSITY   (Hungary)

^c CHEMICAL RESEARCH CENTER   (Hungary)

Author keywords

Coumarins; Hydrolysis; Palladium; Pyridazinones; Suzuki reaction

Indexed keywords

2 (1 BENZYL 5 HYDROXY 6 OXO 1,6 DIHYDROPYRIDAZIN 4 YL)BENZALDEHYDE; 2 (2 BENZYL 5 HYDROXY 3 OXO 2,3 DIHYDROPYRIDAZIN 4 YL)BENZALDEHYDE; 2 BENZYL 1H ISOCHROMENO[3,4 D]PYRIDAZINE 1,6(2H)DIONE; 3 BENZYL 3H ISOCHROMENO[3,4 D]PYRIDAZINE 4,6 DIONE; BENZALDEHYDE DERIVATIVE; PERMANGANATE POTASSIUM; PYRIDAZINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; HYDROLYSIS; LACTONIZATION; OXIDATION; PRIORITY JOURNAL; SYNTHESIS;

LATEOLABRAX JAPONICUS;

EID: 0037175565     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01285-1     Document Type: Article

References (24)

1. For Suzuki arylations on chloropyridazin-3(2H)-ones see: (a) Maes, B. U. W.; R'kyek, O.; Košmrlj, J.; Lemière, G. L. F.; Esmans, E.; Rozenski, J.; Dommisse, R. A.; Haemers, A. Tetrahedron 2001, 57, 1323-1330. (b) Maes, B. U. W.; Košmrjl, J.; Lemière, G. L. F. J. Heterocycl. Chem. 2002, 39, 535-543. (c) Riedl, Z.; Maes, B. U. W.; Monsieurs, K.; Lemière, G. L. F.; Mátyus, P.; Hajós, G. Tetrahedron 2002, 58, 5645-5650. For Suzuki Arylations on Bromopyridazin-3(2H)-ones see: (d) Coelho, A.; Sotelo, E.; Estévez, I.; Raviña, E. Synthesis 2001, 871-876. (e) Li, C. S.; Gauthier, J. Y.; Lau, C. K.; Therein, M. US Patent 6004960, 1999. for suzuki arylations on iodopyridazin-3(2H)-ones see: (f) krajsovszky, g.; mátyus, p.; riedl, z.; csányi, d.; hajós, g. heterocycles 2001, 55, 1105-1111.
2. For Suzuki arylations on chloropyridazin-3(2H)-ones see: (a) Maes, B. U. W.; R'kyek, O.; Košmrlj, J.; Lemière, G. L. F.; Esmans, E.; Rozenski, J.; Dommisse, R. A.; Haemers, A. Tetrahedron 2001, 57, 1323-1330. (b) Maes, B. U. W.; Košmrjl, J.; Lemière, G. L. F. J. Heterocycl. Chem. 2002, 39, 535-543. (c) Riedl, Z.; Maes, B. U. W.; Monsieurs, K.; Lemière, G. L. F.; Mátyus, P.; Hajós, G. Tetrahedron 2002, 58, 5645-5650. For Suzuki Arylations on Bromopyridazin-3(2H)-ones see: (d) Coelho, A.; Sotelo, E.; Estévez, I.; Raviña, E. Synthesis 2001, 871-876. (e) Li, C. S.; Gauthier, J. Y.; Lau, C. K.; Therein, M. US Patent 6004960, 1999. for suzuki arylations on iodopyridazin-3(2H)-ones see: (f) krajsovszky, g.; mátyus, p.; riedl, z.; csányi, d.; hajós, g. heterocycles 2001, 55, 1105-1111.
3. For Suzuki arylations on chloropyridazin-3(2H)-ones see: (a) Maes, B. U. W.; R'kyek, O.; Košmrlj, J.; Lemière, G. L. F.; Esmans, E.; Rozenski, J.; Dommisse, R. A.; Haemers, A. Tetrahedron 2001, 57, 1323-1330. (b) Maes, B. U. W.; Košmrjl, J.; Lemière, G. L. F. J. Heterocycl. Chem. 2002, 39, 535-543. (c) Riedl, Z.; Maes, B. U. W.; Monsieurs, K.; Lemière, G. L. F.; Mátyus, P.; Hajós, G. Tetrahedron 2002, 58, 5645-5650. For Suzuki Arylations on Bromopyridazin-3(2H)-ones see: (d) Coelho, A.; Sotelo, E.; Estévez, I.; Raviña, E. Synthesis 2001, 871-876. (e) Li, C. S.; Gauthier, J. Y.; Lau, C. K.; Therein, M. US Patent 6004960, 1999. for suzuki arylations on iodopyridazin-3(2H)-ones see: (f) krajsovszky, g.; mátyus, p.; riedl, z.; csányi, d.; hajós, g. heterocycles 2001, 55, 1105-1111.
4. For Suzuki arylations on chloropyridazin-3(2H)-ones see: (a) Maes, B. U. W.; R'kyek, O.; Košmrlj, J.; Lemière, G. L. F.; Esmans, E.; Rozenski, J.; Dommisse, R. A.; Haemers, A. Tetrahedron 2001, 57, 1323-1330. (b) Maes, B. U. W.; Košmrjl, J.; Lemière, G. L. F. J. Heterocycl. Chem. 2002, 39, 535-543. (c) Riedl, Z.; Maes, B. U. W.; Monsieurs, K.; Lemière, G. L. F.; Mátyus, P.; Hajós, G. Tetrahedron 2002, 58, 5645-5650. For Suzuki Arylations on Bromopyridazin-3(2H)-ones see: (d) Coelho, A.; Sotelo, E.; Estévez, I.; Raviña, E. Synthesis 2001, 871-876. (e) Li, C. S.; Gauthier, J. Y.; Lau, C. K.; Therein, M. US Patent 6004960, 1999. for suzuki arylations on iodopyridazin-3(2H)-ones see: (f) krajsovszky, g.; mátyus, p.; riedl, z.; csányi, d.; hajós, g. heterocycles 2001, 55, 1105-1111.
5. For Suzuki arylations on chloropyridazin-3(2H)-ones see: (a) Maes, B. U. W.; R'kyek, O.; Košmrlj, J.; Lemière, G. L. F.; Esmans, E.; Rozenski, J.; Dommisse, R. A.; Haemers, A. Tetrahedron 2001, 57, 1323-1330. (b) Maes, B. U. W.; Košmrjl, J.; Lemière, G. L. F. J. Heterocycl. Chem. 2002, 39, 535-543. (c) Riedl, Z.; Maes, B. U. W.; Monsieurs, K.; Lemière, G. L. F.; Mátyus, P.; Hajós, G. Tetrahedron 2002, 58, 5645-5650. For Suzuki Arylations on Bromopyridazin-3(2H)-ones see: (d) Coelho, A.; Sotelo, E.; Estévez, I.; Raviña, E. Synthesis 2001, 871-876. (e) Li, C. S.; Gauthier, J. Y.; Lau, C. K.; Therein, M. US Patent 6004960, 1999. for suzuki arylations on iodopyridazin-3(2H)-ones see: (f) krajsovszky, g.; mátyus, p.; riedl, z.; csányi, d.; hajós, g. heterocycles 2001, 55, 1105-1111.
6. For Suzuki arylations on chloropyridazin-3(2H)-ones see: (a) Maes, B. U. W.; R'kyek, O.; Košmrlj, J.; Lemière, G. L. F.; Esmans, E.; Rozenski, J.; Dommisse, R. A.; Haemers, A. Tetrahedron 2001, 57, 1323-1330. (b) Maes, B. U. W.; Košmrjl, J.; Lemière, G. L. F. J. Heterocycl. Chem. 2002, 39, 535-543. (c) Riedl, Z.; Maes, B. U. W.; Monsieurs, K.; Lemière, G. L. F.; Mátyus, P.; Hajós, G. Tetrahedron 2002, 58, 5645-5650. For Suzuki Arylations on Bromopyridazin-3(2H)-ones see: (d) Coelho, A.; Sotelo, E.; Estévez, I.; Raviña, E. Synthesis 2001, 871-876. (e) Li, C. S.; Gauthier, J. Y.; Lau, C. K.; Therein, M. US Patent 6004960, 1999. for suzuki arylations on iodopyridazin-3(2H)-ones see: (f) krajsovszky, g.; mátyus, p.; riedl, z.; csányi, d.; hajós, g. heterocycles 2001, 55, 1105-1111.
7. Miyaura N., Yanagi T., Suzuki A. Synth. Commun. 11:1981;513-519.
8. Examples on alkaline hydrolysis of methoxy substituted pyridazin-3(2H)-ones: (a) Konečnú V. Chem. Zvesti. 30:1976;663-673 (b) Takaya M., Yamashita T., Ozeki K. Yakugaku Zasshi. 98:1978;413-417 (c) Cho S.D., Chung J.W., Choi W.Y., Kim S.K., Yoon Y.J. J. Heterocycl. Chem. 31:1994;1199-1208 (d) Cho S.D., Choi W.Y., Yoon Y.J. J. Heterocycl. Chem. 33:1996;1579-1582 (e) Kappe T. J. Heterocycl. Chem. 35:1998;1111-1122 (f) Brown D.J. The Pyridazines. Supplement I. 2000;Wiley. p 255.
9. Examples on alkaline hydrolysis of methoxy substituted pyridazin-3(2H)-ones: (a) Konečnú V. Chem. Zvesti. 30:1976;663-673 (b) Takaya M., Yamashita T., Ozeki K. Yakugaku Zasshi. 98:1978;413-417 (c) Cho S.D., Chung J.W., Choi W.Y., Kim S.K., Yoon Y.J. J. Heterocycl. Chem. 31:1994;1199-1208 (d) Cho S.D., Choi W.Y., Yoon Y.J. J. Heterocycl. Chem. 33:1996;1579-1582 (e) Kappe T. J. Heterocycl. Chem. 35:1998;1111-1122 (f) Brown D.J. The Pyridazines. Supplement I. 2000;Wiley. p 255.
10. Examples on alkaline hydrolysis of methoxy substituted pyridazin-3(2H)-ones: (a) Konečnú V. Chem. Zvesti. 30:1976;663-673 (b) Takaya M., Yamashita T., Ozeki K. Yakugaku Zasshi. 98:1978;413-417 (c) Cho S.D., Chung J.W., Choi W.Y., Kim S.K., Yoon Y.J. J. Heterocycl. Chem. 31:1994;1199-1208 (d) Cho S.D., Choi W.Y., Yoon Y.J. J. Heterocycl. Chem. 33:1996;1579-1582 (e) Kappe T. J. Heterocycl. Chem. 35:1998;1111-1122 (f) Brown D.J. The Pyridazines. Supplement I. 2000;Wiley. p 255.
11. Examples on alkaline hydrolysis of methoxy substituted pyridazin-3(2H)-ones: (a) Konečnú V. Chem. Zvesti. 30:1976;663-673 (b) Takaya M., Yamashita T., Ozeki K. Yakugaku Zasshi. 98:1978;413-417 (c) Cho S.D., Chung J.W., Choi W.Y., Kim S.K., Yoon Y.J. J. Heterocycl. Chem. 31:1994;1199-1208 (d) Cho S.D., Choi W.Y., Yoon Y.J. J. Heterocycl. Chem. 33:1996;1579-1582 (e) Kappe T. J. Heterocycl. Chem. 35:1998;1111-1122 (f) Brown D.J. The Pyridazines. Supplement I. 2000;Wiley. p 255.
12. Examples on alkaline hydrolysis of methoxy substituted pyridazin-3(2H)-ones: (a) Konečnú V. Chem. Zvesti. 30:1976;663-673 (b) Takaya M., Yamashita T., Ozeki K. Yakugaku Zasshi. 98:1978;413-417 (c) Cho S.D., Chung J.W., Choi W.Y., Kim S.K., Yoon Y.J. J. Heterocycl. Chem. 31:1994;1199-1208 (d) Cho S.D., Choi W.Y., Yoon Y.J. J. Heterocycl. Chem. 33:1996;1579-1582 (e) Kappe T. J. Heterocycl. Chem. 35:1998;1111-1122 (f) Brown D.J. The Pyridazines. Supplement I. 2000;Wiley. p 255.
13. Examples on alkaline hydrolysis of methoxy substituted pyridazin-3(2H)-ones: (a) Konečnú V. Chem. Zvesti. 30:1976;663-673 (b) Takaya M., Yamashita T., Ozeki K. Yakugaku Zasshi. 98:1978;413-417 (c) Cho S.D., Chung J.W., Choi W.Y., Kim S.K., Yoon Y.J. J. Heterocycl. Chem. 31:1994;1199-1208 (d) Cho S.D., Choi W.Y., Yoon Y.J. J. Heterocycl. Chem. 33:1996;1579-1582 (e) Kappe T. J. Heterocycl. Chem. 35:1998;1111-1122 (f) Brown D.J. The Pyridazines. Supplement I. 2000;Wiley. p 255.
14. R'kyek O., Maes B.U.W., Jonckers T.H.M., Lemière G.L.F., Dommisse R.A. Tetrahedron. 57:2001;10009-10016.
15. 1e yielded a mixture of 2-benzyl-4-bromo-5-(4-methylthiophenyl)pyridazin-3(2H)-one (30%) and 2-benzyl-4,5-bis-(4-methylthiophenyl)-pyridazin-3(2H)-one (3%). Although formation of the monoarylated compound is favoured only a low yield was obtained. Moreover, it is very hard to separate 2-benzyl-4-bromo-5-(4-methylthiophenyl)pyridazin-3(2H)-one from the minor compound 2-benzyl-4,5-bis-(4-methylthiophenyl)pyridazin-3(2H)-one due to similar polarity properties.
16. 3 see: (a) Kaji, K.; Nagashima, H.; Oda, H.; Chem. Pharma. Bull. 1984, 32, 1423-1432. (b) Haider, N.; Heinisch, G. J. Chem. Soc., Perkin Trans. 1 1986, 169-172. (c) Haider, N.; Heinisch, G. J. Chem. Soc., Perkin Trans. 1 1988, 401-405. (d) Haider, N.; Heinisch, G.; Volf, I. Heterocycles 1989, 29, 1309-1316. (e) Zára-Kaczián, E.; Mátyus, P. Heterocycles 1993, 36, 519-528. (f) see ref. 1c.
17. 3 see: (a) Kaji, K.; Nagashima, H.; Oda, H.; Chem. Pharma. Bull. 1984, 32, 1423-1432. (b) Haider, N.; Heinisch, G. J. Chem. Soc., Perkin Trans. 1 1986, 169-172. (c) Haider, N.; Heinisch, G. J. Chem. Soc., Perkin Trans. 1 1988, 401-405. (d) Haider, N.; Heinisch, G.; Volf, I. Heterocycles 1989, 29, 1309-1316. (e) Zára-Kaczián, E.; Mátyus, P. Heterocycles 1993, 36, 519-528. (f) see ref. 1c.
18. 3 see: (a) Kaji, K.; Nagashima, H.; Oda, H.; Chem. Pharma. Bull. 1984, 32, 1423-1432. (b) Haider, N.; Heinisch, G. J. Chem. Soc., Perkin Trans. 1 1986, 169-172. (c) Haider, N.; Heinisch, G. J. Chem. Soc., Perkin Trans. 1 1988, 401-405. (d) Haider, N.; Heinisch, G.; Volf, I. Heterocycles 1989, 29, 1309-1316. (e) Zára-Kaczián, E.; Mátyus, P. Heterocycles 1993, 36, 519-528. (f) see ref. 1c.
19. 3 see: (a) Kaji, K.; Nagashima, H.; Oda, H.; Chem. Pharma. Bull. 1984, 32, 1423-1432. (b) Haider, N.; Heinisch, G. J. Chem. Soc., Perkin Trans. 1 1986, 169-172. (c) Haider, N.; Heinisch, G. J. Chem. Soc., Perkin Trans. 1 1988, 401-405. (d) Haider, N.; Heinisch, G.; Volf, I. Heterocycles 1989, 29, 1309-1316. (e) Zára-Kaczián, E.; Mátyus, P. Heterocycles 1993, 36, 519-528. (f) see ref. 1c.
20. 3 see: (a) Kaji, K.; Nagashima, H.; Oda, H.; Chem. Pharma. Bull. 1984, 32, 1423-1432. (b) Haider, N.; Heinisch, G. J. Chem. Soc., Perkin Trans. 1 1986, 169-172. (c) Haider, N.; Heinisch, G. J. Chem. Soc., Perkin Trans. 1 1988, 401-405. (d) Haider, N.; Heinisch, G.; Volf, I. Heterocycles 1989, 29, 1309-1316. (e) Zára-Kaczián, E.; Mátyus, P. Heterocycles 1993, 36, 519-528. (f) See Ref. 1c.
21. 3 see: (a) Kaji, K.; Nagashima, H.; Oda, H.; Chem. Pharma. Bull. 1984, 32, 1423-1432. (b) Haider, N.; Heinisch, G. J. Chem. Soc., Perkin Trans. 1 1986, 169-172. (c) Haider, N.; Heinisch, G. J. Chem. Soc., Perkin Trans. 1 1988, 401-405. (d) Haider, N.; Heinisch, G.; Volf, I. Heterocycles 1989, 29, 1309-1316. (e) Zára-Kaczián, E.; Mátyus, P. Heterocycles 1993, 36, 519-528. (f) See Ref. 1c.
22. Kmetic M., Stanovnik B., Tišler M., Kappe T. Heterocycles. 35:1993;1331-1339.
23. Mátyus P., Fuji K., Tanaka K. Heterocycles. 37:1994;171-174.
24. Toplak R., Selic L., Soršak G., Stanovnik B. Heterocycles. 45:1997;555-565.