A one-pot strategy for regioselective synthesis of 6-aryl-3-oxo-2,3-dihydropyridazine-4-carbohydrazides
A simple and efficient method for the synthesis of 6-aryl-3-oxo-2,3-dihydropyridazine-4-carbohydrazide derivatives was developed. The synthesis was achieved via one-pot multicomponent reaction of arylglyoxals, dialkylmalonates, and hydrazine hydrate in pyridine at room temperature. This procedure features high regioselectivity, generally good to excellent yields, the use of easily available starting materials, and operational simplicity. This chemistry provides an efficient and promising synthetic strategy for diversity-oriented construction of the 6-arylpyridazinone skeleton.
A one-pot strategy for regioselective synthesis of 6-aryl-3-oxo-2,3-dihydropyridazine-4-carbohydrazides
A simple and efficient method for the synthesis of 6-aryl-3-oxo-2,3-dihydropyridazine-4-carbohydrazide derivatives was developed. The synthesis was achieved via one-pot multicomponent reaction of arylglyoxals, dialkylmalonates, and hydrazine hydrate in pyridine at room temperature. This procedure features high regioselectivity, generally good to excellent yields, the use of easily available starting materials, and operational simplicity. This chemistry provides an efficient and promising synthetic strategy for diversity-oriented construction of the 6-arylpyridazinone skeleton.
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- (a) Lebel, H.; Ladjel, C.; Brethous, L. J. Am. Chem. Soc. 2007, 129, 13321–13326; (b) Chapman, C. J.; Frost, C. G. Synthesis 2007, 1–21; (c) Nicolaou, K. C.; Edmonds, D. J.; Bulger, P. G. Angew. Chem., Int. Ed. 2006, 45, 7134–7186; (d) Pelissier, H. Tetrahedron 2006, 62, 2143–2173; (e) Pellissier, H. Tetrahedron 2006, 62, 1619–1665; (f) Guo, H. C.; Ma, J. A. Angew. Chem., Int. Ed. 2006, 45, 354–366; (g) Domling, A. Chem. Rev. 2006, 106, 17–89; (h) Broadwater, S. J.; Roth, S. L.; Price, K. E.; Kobaslija, M.; McQuade, D. T. Org. Biomol. Chem. 2005, 3, 2899–2906; (i) Ulaczyk-Lesanko, A.; Hall, D. G. Curr. Opin. Chem. Biol. 2005, 9, 266–276; (j) Ramon, D. J.; Yus, M. Angew. Chem., Int. Ed. 2005, 44, 1602–1634; (k) Tietze, L. F.; Rackelmann, N. Pure Appl. Chem. 2004, 76, 1967–1983; (l) Catellani, M. Synlett 2003, 298–313; (m) Pamies, O.; B¨ ackvall, J. E. Chem. Rev. 2003, 103, 3247–3261; (n) McCarroll, A. J.; Walton, J. C. J. Chem. Soc., Perkin Trans. 1 2001, 3215–3229; (o) Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195–206; (p) Tietze, L. F. Chem. Rev. 1996, 96, 115–136; (q) Sheldon, R. A. Chem. Commun. 2008, 29, 3352–3365; (r) Ekoue-Kovi, K.; Wolf, C. Chem. Eur. J. 2008, 14, 6302–6315; (s) Yu, X.; Wang, W. Org. Biomol. Chem. 2008, 6, 2037–2046.
- (a) Ajamian, A.; Gleason, J. L. Angew. Chem., Int. Ed. 2004, 43, 3754–3760; (b) Fogg, D. E.; dos Santos, E. N. Coord. Chem. Rev. 2004, 248, 2365–2379; (c) Seigal, B. A.; Fajardo, C.; Snapper, M. L. J. Am. Chem. Soc. 2005, 127, 16329–16332.
- (a) Pokhodylo, N. T.; Matiychuk, V. S.; Obushak, M. D. J. Comb. Chem. 2009, 11, 481–485; (b) Ghahremanzadeh, R.; Sayyafi, M.; Ahadi, S.; Bazgir, A. J. Comb. Chem. 2009, 11, 393–396; (c) Zhang, L.; Lushington, G. H.; Neuenswander, B.; Hershberger, J. C.; Malinakova, H. C. J. Comb. Chem. 2008, 10, 285–302; (d) Tu, S. J.; Zhang, X. H.; Han, Z. G.; Cao, X. D.; Wu, S. S.; Yan, S.; Hao, W. J.; Zhang, G.; Ma, N. J. Comb. Chem. 2009, 11, 428–432; (e) Wang, X. S.; Li, Q.; Wu, J. R.; Tu, S. J. J. Comb. Chem. 2009, 11, 433–437.
- (a) Domling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168–3210; (b) Shaabani, A.; Seyyedhamzeh, M.; Maleki, A.; Behnam, M.; Rezazadeh, F. Tetrahedron Lett. 2009, 50, 2911–2913; (c) Adib, M.; Sheibani, E.; Bijanzadeh, H. R.; Zhu, L. G. Tetrahedron 2008, 64, 10681–10686; (d) Sunderhaus, J. D.; Martin, S. F. Chem. Eur. J. 2009, 15, 1300–1308.
- (a) Jiang, B.; Tu, S. J.; Kaur, P.; Wever W.; Li, G. J. Am. Chem. Soc., 2009, 131, 11660–11661; (b) Jiang, Li, B.; Shi, C. F.; Tu,S.–J.; Parminder, K.; Walter, W.; Li, G. J. Org. Chem., 2010, 75, 2962–2965.
- (a) Enders, D.; Huttl, M. R. M.; Grondal, C.; Raabe, G. Nature 2006, 441, 861–863; (b) Tietze, L. F.; Haunert, F. In Stimulating Concepts in Chemistry, Wiley-VCH: Weinheim, Germany, 2000, pp. 39–64.
- Toure, B. B.; Hall, D. G. Chem. Rev. 2009, 109, 4439–4486.
- Coelho, A.; Sotelo, E.; Ravina, E. Tetrahedron 2003, 59, 2477–2484.
- Monge, A.; Parrado, P.; Font, M.; Alvarez, E. F. J. Med. Chem. 1987, 30, 1029–1035.
- Rubat, C.; Coudert, P.; Refouvelet, B.; Tronche, P.; Bastide, P. Chem. Pharm. Bull. 1990, 38, 3009–3013.
- Sircar, I.; Weishaar, R. E.; Kobylarz, D.; Moos, W. H.; Bristol, J. A. J. Med. Chem. 1987, 30, 1955–1962.
- Longo, J. G.; Verde, I.; Castro, M. E. J. Pharm. Sci. 1993, 82, 286–290.
- Akahane, A.; Katayama, H.; Mitsunaga, T. J. Med. Chem. 1999, 42, 779–783.
- Livermone, D. G. H.; Bethell, R. C.; Cammack, N. J. Med. Chem. 1993, 36, 3784–3794.
- Malinka, W.; Redzicka, A.; Lozach, O. Farmaco 2004, 59, 457–462.
- Abouzid, K.; Hakeem, M. A.; Khalil, O.; Maklad, Y. Bioorg. Med. Chem. 2008, 16, 382–389.
- Combs, D. W.; Rampulla, M. S.; Bell, S. C.; Klaubert, D. H.; Tobia, A. J.; Falotico, R.; Haertlein, B.; Weiss, C. L.; Moore, J. B. J. Med. Chem. 1990, 22, 380–386.
- Robertson, D. W.; Jones, N. D.; Krushinski, J. H.; Pollock, G. D.; Swartzendruber, J. K.; Scott Hayes, J. J. Med. Chem. 1987, 30, 623–627.
- Archan, S.; Toller, W. Curr. Opin. Anesthesiol. 2008, 21, 78–84.
- Sotelo, E.; Coelho, A.; Ravina, E. Tetrahedron Lett. 2003, 44, 4459–4462.
- Siddiqui, A. A.; Ahmad, S. R.; Hussain, S. A. Acta. Pol. Pharm. 2008, 64, 223–228.
- Siddiqui, A. A.; Kushnoor, A.; Wani, S. M. Ind. J. Heterocycl. Chem. 2004, 13, 257–260.
- Stevenson, T. M.; Crouse, B. A.; Thieu, T. V.; Gebreysus, C.; Finkelstein, B. L; Sethuraman, M. R.; Dubas-Cordery, C. M.; Piotrowski, D. L. J. Heterocycl. Chem. 2005, 42, 427–435.
- Kerdesky, F. A.; Leanna, M. R.; Zhang, J.; Li, W.; Lallaman, J. E.; Ji, J.; Morton, H. E. Org. Process Res. Dev. 2006, 10, 512–517.
- Chiou, G. C. Y. Drugs Future 1999, 24, 979–990.
- Gong, Y.; Barbay, J. K.; Byatkin, A. B.; Miskowski, T. A.; Kimball, E. S.; Prouty, S. M.; Fisher, M. C.; Santulli, R. J.; Schneider, C. R.; Wallace, N. H.; Ballentine, S. A.; Hageman, W. E.; Masucci, J. A.; Maryanoff, B. E.; Damiano, B. P.; Andrade-Gordon, P.; Hlasta, D. J.; Hornby, P. J.; He, W. J. Med. Chem. 2006, 49, 3402–3411.
- Chintakunta, V. K.; Akella, V.; Vedula, M. S.; Mamnoor, P. K.; Mishra, P.; Casturi, S. R.; Vangoori, A.; Rajagopalan, R. Eur. J. Med. Chem. 2002, 37, 339–347.
- Li, C. S.; Brideau, C.; Chan, C. C.; Savoie, C.; Claveau, D.; Charleson, S.; Gordon, R.; Greig, G.; Gauthier, J. Y.; Lau, C. K.; Riendeau, D.; Th´erien, M.; Wong, E.; Prasit, P. Bioorg. Med. Chem. Lett. 2003, 13, 597–600.
- Review: Manetti, F.; Corelli, F.; Strappaghetti, F.; Botta, M. Curr. Med. Chem. 2002, 9, 1303–1321.
- For references to the biological activity of arylpyridazinones see: Salives, R.; Dupas, G.; Pl´e, N.; Qu´eguiner, G.; Turck, A.; George, P.; Servin, M.; Frost, J.; Almario, A.; Li, A. J. Comb. Chem. 2005, 7, 414–420.
- Dragovich, P. S.; Blazel, J. K.; Ellis, D. A.; Han, Q.; Kamran, R.; Kissinger, C. R.; Webber, S. E.; Showalter, R. E.; Shah, A. M.; Tsan, M.; Patel, R. A.; Thompson, P. A.; Lebrun, L. A.; Hou, H. J.; Kamran, R.; Sergeeva, M. V.; Bartkowski, D. M.; Nolan, T. G.; Norris, D. A.; Khandurina, J.; Brooks, J.; Okamoto, E.; Kirkovsky, L. Bioorg. Med. Chem. Lett. 2008, 18, 5635–5639.
- (a) Zhou, Y.; Webber, S. E.; Murphy, D. E.; Li, L.-S.; Dragovich, P. S.; Tran, C. V.; Sun, Z.; Ruebsam, F.; Shah, A. M.; Tsan, M.; Showalter, R. E.; Patel, R.; Li, B.; Zhao, Q.; Han, Q.; Hermann, T.; Kissinger, C. R.; LeBrun, L.; Sergeeva, M. V.; Kirkovsky, L. Bioorg. Med. Chem. Lett. 2008, 18, 1413–1418; (b) Zhou, Y.; Li, L.-S.; Dragovich, P. S.; Murphy, D. E.; Tran, C. V.; Ruebsam, F.; Webber, S. E.; Shah, A. M.; Tsan, M.; Averill, A.; Showalter, R. E.; Patel, R.; Han, Q.; Zhao, Q.; Hermann, T.; Kissinger, C. R.; LeBrun, L.; Sergeeva, M. V. Bioorg. Med. Chem. Lett. 2008, 18, 1419–1424; (c) Li, L.-S.; Zhou, Y.; Murphy, D. E.; Stankovic, N.; Zhao, J.; Dragovich, P. S.; Bertolini, T.; Sun, Z.; Ayida, B.; Tran, C. V.; Ruebsam, F.; Webber, S. E.; Shah, A. M.; Tsan, M.; Showalter, R. E.; Patel, R.; LeBrun, L. A.; Bartkowski, D. M.; Nolan, T. G.; Norris, D. A.; Kamran, R.; Brooks, J.; Sergeeva, M. V.; Kirkovsky, L.; Zhao, Q.; Kissinger, C. R. Bioorg. Med. Chem. Lett. 2008, 18, 3446–3455; (d) Sergeeva, M. V.; Zhou, Y.; Bartkowski, D. M.; Nolan, T. G.; Norris, D. A.; Okamoto, E.; Kirkovsky, L.; Kamran, R.; LeBrun, L. A.; Tsan, M.; Patel, R.; Shah, A. M.; Lardy, M.; Gobbi, A.; Li, L.-S.; Zhao, J.; Bertolini, T.; Stankovic, N.; Sun, Z.; Murphy, D. E.; Webber, S. E.; Dragovich, P. S. Bioorg. Med. Chem. Lett. 2008, 18, 3421–3426.
- (a) Hutchinson, D. K.; Rosenberg, T.; Klein, L. L.; Bosse, T. D.; Larson, D. P.; He, W.; Jiang, W. W.; Kati, W. M.; Kohlbrenner, W. E.; Liu, Y.; Masse, S. V.; Middleton, T.; Molla, A.; Montgomery, D. A.; Beno, D. W. A.; Stewart, K. D.; Stoll, V. S.; Kempf, D. J. Bioorg. Med. Chem. Lett. 2008, 18, 3887–3890; (b) Bosse, T. D.; Larson, D. P.; Wagner, R.; Hutchinson, D. K.; Rockway, T. W.; Kati, W. M.; Liu, Y.; Masse, S.; Middleton, T.; Mo, H.; Montgomery, D.; Jiang, W.; Koev, G.; Kempf, D. J.; Molla, A. Bioorg. Med. Chem. Lett. 2008, 18, 568–570; (c) Krueger, A. C.; Madigan, D. L.; Green, B. E.; Hutchinson, D. K.; Jiang, W. W.; Kati, W. M.; Liu, Y.; Maring, C. J.; Masse, S. V.; McDaniel, K. F.; Middleton, T. R.; Mo, H.; Molla, A.; Montgomery, D. A.; Ng, T. I.; Kempf, D. J. Bioorg. Med. Chem. Lett. 2007, 17, 2289–2292; (d) Tedesco, R.; Shaw, A. N.; Bambal, R.; Chai, D.; Concha, N. O.; Darcy, M. G.; Dhanak, D.; Fitch, D. M.; Gates, A.; Gerhardt, W. G.; Halegoua, D. L.; Han, C.; Hofmann, G. A.; Johnston, V. K.; Kaura, A. C.; Liu, N.; Keenan, R. M.; Goerke, J. L.; Sarisky, R. T.; Wiggall, K. J.; Zimmerman, M. N.; Duffy, K. J. J. Med. Chem. 2006, 49, 971–983; (e) Pratt, J. K.; Donner, P.; McDaniel, K. F.; Maring, C. J.; Kati, W. M.; Mo, H.; Middleton, T.; Liu, Y.; Ng, T.; Xie, Q.; Zhang, R.; Montgomery, D.; Molla, A.; Kempf, D. J.; Kohlbrenner, W. Bioorg. Med. Chem. Lett. 2005, 15, 1577–1582.
- Curran, W. V.; Ross, A. J. Med. Chem. 1974, 17, 273–281.
- Demirayak, S.; Karaburun, A. C.; Beis, R. Eur. J. Med. Chem. 2004, 39, 1089–1095.
- Siddiqui, A. A.; Wani, S. M. Ind. J. Chem. 2004, 43B, 1574–1579.
- Siddiqui, A. A.; Mishra, R.; Shaharyar, M. Eur. J. Med. Chem. 2010, 45, 2283–2290.
- Overend, W. G.; Wiggins, L. F. J. Chem. Soc. 1947, 239–244.
- Albright, J. D.; McEvoy, F. J.; Moran, D. B. J. Heterocycl. Chem. 1978, 15, 881–892.
- Coates, W. J.; McKillop, A. Synthesis 1993, 334–342.
- Steck, E. A.; Brundage, R. P.; Fletcher, L. T. J. Am. Chem. Soc. 1953, 75, 1117–1119.
- Bourguignon, J. J.; Wermuth, C. G. J. Org. Chem. 1981, 46, 4889–4894.
- Wermuth, C. G.; Schlewer, G.; Bourguignon, J. J.; Maghioros, G.; Bouchet, M. J.; Moire, C.; Kan, J. P.; Worms, P.; Biziere, K. J. Med. Chem. 1989, 32, 528–537.
- Contreras, J. M.; Rival, Y. M.; Chayer, S.; Bourguignon, J. J.; Wermuth, C. G. J. Med. Chem. 1999, 42, 730–741. (a) Khalafy, J.; Rimaz, M.; Ezzati, M.; Prager, R. H. Bull. Korean Chem. Soc. 2012, 33, 2890–2896. (b) Khalafy, J.; Rimaz, M.; Ezzati, M. Curr. Chem. Lett. 2012, 1, 115–122. (c) Khalafy, J.; Rimaz, M.; Panahi, L.; Rabiei, H. Bull. Korean Chem. Soc. 2011, 32, 2428–2432. (d) Rimaz, M.; Khalafy, J. Arkivoc 2010, (ii ), 110–117. (e) Rimaz, M.; Khalafy, J.; Najafi Moghadam, P. Aust. J. Chem. 2010, 63, 1396–1401. (f) Rimaz, M.; Noroozi Pesyan, N.; Khalafy, J. Magn. Reson. Chem. 2010, 48, 276–285. (g) Rimaz, M.; Khalafy, J.; Noroozi Pesyan, N.; Prager, R. H. Aust. J. Chem. 2010, 63, 507–510. (h) Khalafy, J.; Rimaz, M.; Ezzati, M.; Marjani, A. P. Curr. Chem. Lett. 2013, 2, 43–48.
- Perrin, D. D.; Amarego, W. L. F. Purification of Laboratory Chemicals, 3rd ed., Pergamon Press: Oxford, 1988.