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RESEARCH ARTICLE

Two Efficient One-Pot Approaches for Regioselective Synthesis of New 3-Arylpyridazino[4,3-c]quinolin-5(6H)-ones

Mehdi Rimaz
+ Author Affiliations
- Author Affiliations

Department of Chemistry, Payame Noor University, PO Box 19395-3697, Tehran, Iran. Email: rimaz.mehdi@gmail.com

Australian Journal of Chemistry 68(10) 1529-1534 https://doi.org/10.1071/CH15029
Submitted: 20 January 2015  Accepted: 25 March 2015   Published: 23 April 2015

Abstract

Two efficient regioselective approaches for the one-pot synthesis of 3-arylpyridazino[4,3-c]quinolin-5(6H)-one derivatives are reported, by the three-component reaction of arylglyoxal monohydrates, quinoline-2,4-diol, and hydrazinium dihydrochloride or hydrazine hydrate in ethanol and pyridine. In ethanol, the reactions were catalyzed by 1,4-diazobicyclo[2,2,2]octane. The features of both procedures are high regioselectivity, mild reaction conditions, good to high yields, and operational simplicity.


References

[1]  (a) A. Erkkila, I. Majander, P. M. Pihko, Chem. Rev. 2007, 107, 5416.
         | Crossref | GoogleScholarGoogle Scholar | 18072802PubMed |
      (b) S. Laschat, A. Becheanu, T. Bell, A. Baro, Synlett 2005, 2547.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) F. Z. Dörwald, Angew. Chem. Int. Ed. 2003, 42, 1332.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) P. Beak, D. R. Anderson, M. D. Curtis, J. M. Laumer, D. J. Pippel, G. A. Weisenburger, Acc. Chem. Res. 2000, 33, 715.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) A. L. J. Beckwith, Tetrahedron 1981, 37, 3073.
         | Crossref | GoogleScholarGoogle Scholar |

[2]  (a) V. Nair, C. Rajesh, A. U. Vinod, S. Bindu, A. R. Sreekanth, J. S. Mathen, L. Balagopal, Acc. Chem. Res. 2003, 36, 899.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXnsl2nu7k%3D&md5=b9cc74c29173b9c4b5e6df58e6131ff5CAS | 14674781PubMed |
      (b) Y. K. Chen, P. J. Walsh, J. Am. Chem. Soc. 2004, 126, 3702.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) L. F. Tietze, Chem. Rev. 1996, 96, 115.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) X. S. Wang, Q. Li, C. S. Yao, S. J. Tu, Eur. J. Org. Chem. 2008, 3513.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) A. Padwa, S. K. Bur, Tetrahedron 2007, 63, 5341.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) K. C. Nicolaou, D. J. Edmonds, P. G. Bulger, Angew. Chem. Int. Ed. 2006, 45, 7134.
         | Crossref | GoogleScholarGoogle Scholar |
      (g) L. Weber, K. Illgen, M. Almstetter, Synlett 1999, 366.
         | Crossref | GoogleScholarGoogle Scholar |
      (h) A. R. Siamaki, B. A. Arndtsen, J. Am. Chem. Soc. 2006, 128, 6050.
         | Crossref | GoogleScholarGoogle Scholar |
      (i) C. Ma, Y. Yang, Org. Lett. 2005, 7, 1343.
         | Crossref | GoogleScholarGoogle Scholar |
      (j) C. V. Galliford, K. A. Scheidt, J. Org. Chem. 2007, 72, 1811.
         | Crossref | GoogleScholarGoogle Scholar |

[3]  (a) F. Lieby-Muller, T. Constantieux, J. Jean Rodriguez, J. Am. Chem. Soc. 2005, 127, 17176.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXht1WltL%2FK&md5=6379742574418822b352edd84ff9c784CAS | 16332052PubMed |
      (b) D. G. Rivera, L. A. Wessjohann, J. Am. Chem. Soc. 2006, 128, 7122.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) V. A. Chebanov, V. E. Saraev, S. M. Desenko, V. N. Chernenko, I. V. Knyazeva, U. Groth, T. N. Glasnov, C. O. Kappe, J. Org. Chem. 2008, 73, 5110.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) B. Groenendaal, D. J. Vugts, R. F. Schmitz, F. J. J. de Kanter, E. Ruijter, M. B. Groen, R. V. A. Orru, J. Org. Chem. 2008, 73, 719.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) G. Abbiati, A. Arcadi, V. Canevari, L. Capezzuto, E. Rossi, J. Org. Chem. 2005, 70, 6454.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) J. D. Sunderhaus, C. Dockendorff, S. F. Martin, Org. Lett. 2007, 9, 4223.
         | Crossref | GoogleScholarGoogle Scholar |
      (g) V. Nair, R. S. Menon, P. B. Beneesh, V. Sreekumar, S. Bindu, Org. Lett. 2004, 6, 767.
         | Crossref | GoogleScholarGoogle Scholar |
      (h) M. Zhang, H. Jiang, H. Liu, Q. Zhu, Org. Lett. 2007, 9, 4111.
         | Crossref | GoogleScholarGoogle Scholar |
      (i) B. Willy, T. J. J. Muller, Eur. J. Org. Chem. 2008, 4157.
         | Crossref | GoogleScholarGoogle Scholar |

[4]  (a) R. E. Dolle, B. L. Bourdonnec, A. J. Goodman, G. A. Morales, C. J. Thomas, W. Zhang, J. Comb. Chem. 2008, 10, 753.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhtlCns7jI&md5=fe02c2c3f53e8310bce23043050f4ea9CAS | 18991466PubMed |
      (b) R. E. Dolle, B. L. Bourdonnec, A. J. Goodman, G. A. Morales, J. M. Salvino, W. Zhang, J. Comb. Chem. 2007, 9, 855.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) H. Y. Zhou, A. F. Liu, X. F. Li, X. F. Ma, W. Feng, W. Zhang, B. Yan, J. Comb. Chem. 2008, 10, 303.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) W. Zhang, Y. Lu, C. H. Chen, L. Zeng, D. B. Kassel, J. Comb. Chem. 2006, 8, 687.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) S. J. Tu, C. M. Li, G. G. Li, L. J. Cao, Q. Q. Shao, D. X. Zhou, B. Jiang, J. F. Zhou, M. Xia, J. Comb. Chem. 2007, 9, 1144.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) A. M. Song, J. H. Zhang, K. S. Lam, J. Comb. Chem. 2004, 6, 112.
         | Crossref | GoogleScholarGoogle Scholar |
      (g) A. M. Song, J. H. Zhang, C. B. Lebrilla, K. S. Lam, J. Comb. Chem. 2004, 6, 604.
         | Crossref | GoogleScholarGoogle Scholar |
      (h) Q. P. Ding, J. Wu, J. Comb. Chem. 2008, 10, 541.
         | Crossref | GoogleScholarGoogle Scholar |
      (i) W. Sun, Q. P. Ding, X. Y. Sun, R. H. Fan, J. Wu, J. Comb. Chem. 2007, 9, 690.
         | Crossref | GoogleScholarGoogle Scholar |
      (j) M. Li, Z. Q. Zuo, L. R. Wen, S. W. Wang, J. Comb. Chem. 2008, 10, 436.
         | Crossref | GoogleScholarGoogle Scholar |
      (k) M. Li, E. T. Sun, L. R. Wen, J. H. Sun, Y. F. Li, H. Z. Yang, J. Comb. Chem. 2007, 9, 903.
         | Crossref | GoogleScholarGoogle Scholar |

[5]  (a) Z. Wang, L. Zhou, K. El-Boubbou, X. S. Ye, X. Huang, J. Org. Chem. 2007, 72, 6409.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXnvFGntLk%3D&md5=b3f7f3ebf2a2c805d0ab48a53b0859c6CAS | 17658849PubMed |
      (b) M. M. Heravi, B. Baghernejad, H. A. Oskooie, R. Hekmatshoar, Tetrahedron Lett. 2008, 49, 6101.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) M. Umkehrer, J. Kolb, C. Burdack, W. Hiller, Synlett 2005, 79.
         | Crossref | GoogleScholarGoogle Scholar |

[6]  (a) H. Fan, J. Peng, M. T. Hamann, J. F. Hu, Chem. Rev. 2008, 108, 264.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhsVCrsLvO&md5=7cbfa2a575da2e31d0073478b2b89e73CAS | 18095718PubMed |
      (b) C. Bailly, Curr. Med. Chem.: Anti-Cancer Agents 2004, 4, 363.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) B. Yao, M. R. Prinsep, B. K. Nicholson, D. P. Gordon, J. Nat. Prod. 2003, 66, 1074.
         | Crossref | GoogleScholarGoogle Scholar |

[7]  T. M. Frimurer, T. Ulven, T. Hoegberg, P. K. Norregaard, P. B. Little, J. M. Receveur, Int. Patent WO 2004052371 A2 2004.

[8]  B. Leblond, S. Petit, V. Picard, T. Taverne, F. Schweighoffer, Int. Patent WO 2004076445 A2 2004.

[9]  I. Murakami-Kubo, K. Doh-ura, K. Ishikawa, S. Kawatake, K. Sasaki, J. I. Kira, S. Ohta, T. Iwaki, J. Virol. 2004, 78, 1281.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXmsFSqsg%3D%3D&md5=81c0706c02cf2ec94db424bde7baa110CAS | 14722283PubMed |

[10]  A. Miwa, T. Yoshino, T. Osawa, T. Sakai, T. Shimizu, Y. Fujiwara, Int. Patent WO 2003033472 A1 2003.

[11]  D. T. Davies, G. E. Jones, A. P. Lightfoot, R. E. Markwell, N. D. Pearson, Int. Patent WO 2002008224 A1 2002.

[12]  L. Pitarch, R. Coronas, J. Mallol, Eur. J. Med. Chem. 1974, 9, 644.
         | 1:CAS:528:DyaE2MXksFeiu70%3D&md5=17e8ca525c95434ec54939e72d04ad47CAS |

[13]  R. Herter, H. Engler, P. Morsdorf, H. Schickaneder, V. Pfahlert, K. H. Ahrens, Eur. Pat. Appl. EP 327800 1989.

[14]  Y. Nomoto, H. Takai, T. Ohno, K. Kubo, Eur. Pat. Appl. EP 326307 1989.

[15]  R. A. Slater, W. Howson, G. T. G. Swayne, E. M. Taylor, D. R. Reavill, J. Med. Chem. 1988, 31, 345.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1cXls1Shtw%3D%3D&md5=b44f4a3b3f32ef85c48f97644500a48dCAS | 2892934PubMed |

[16]  R. Buchman, J. A. Scozzie, Z. S. Ariyan, R. D. Heilman, D. J. Rippin, W. J. Pyne, L. J. Powers, R. J. Matthews, J. Med. Chem. 1980, 23, 1398.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL3cXmtl2gtrg%3D&md5=80025a9b5e7fd0cdb289315d11fd4ce9CAS | 7452694PubMed |

[17]  F. Rohet, C. Rubat, P. Coudert, E. Albuisson, J. Couquelet, Chem. Pharm. Bull. (Tokyo) 1996, 44, 980.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28Xjt1GitLk%3D&md5=5d3c9ec71d0e0ff8ebddac3705eb29baCAS | 8689727PubMed |

[18]  A. Ishida, K. Honma, M. Tanifuji, N. Nishiyama, F. Okumura, Jpn. Kokai Tokkyo Koho JP 9071535 1997.

[19]  A. Ishida, K. Honma, M. Tanifuji, N. Nishiyama, F. Okumura, Jpn. Kokai Tokkyo Koho JP 9071534 1997.

[20]  A. Ishida, K. Honma, M. Yato, S. Nishiyama, F. Okumura, Eur. Pat. Appl. EP 661274 1995.

[21]  A. Ishida, K. Honma, M. Yato, S. Nishiyama, F. Okumura, Eur. Pat. Appl. EP 661273 1995.

[22]  H. Okushima, A. Narimatsu, M. Kobayashi, R. Furuya, K. Tsuda, Y. Kitada, J. Med. Chem. 1987, 30, 1157.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2sXkt1egsrk%3D&md5=a545ee685f19a6bcd0b94ca6b21c64afCAS | 3599022PubMed |

[23]  A. Montero-Lastres, N. Fraiz, R. Laguna, E. Cano, I. Estevez, Biol. Pharm. Bull. 1999, 22, 1376.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXitlai&md5=5cf655c792b3a92571a6072347c5ccb9CAS | 10746173PubMed |

[24]  J. M. Contreras, Y. M. Rival, S. Chayer, J. J. Bourguignon, C. G. Wermuth, J. Med. Chem. 1999, 42, 730.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXosVyntQ%3D%3D&md5=94dc97e3707e4515b7d4c1d8d6a11de3CAS | 10052979PubMed |

[25]  M. P. Giovannoni, V. D. Piaz, B. M. Kwon, M. K. Kim, Y. K. Kim, L. Toma, D. Barlocco, F. Bernini, M. Canavesi, J. Med. Chem. 2001, 44, 4292.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXnslOhsbk%3D&md5=ade9f4af76403e9ee9f452cd69d5d467CAS | 11708931PubMed |

[26]  B. L. Mylari, S. J. Armento, D. A. Beebe, E. L. Conn, J. B. Coutcher, M. S. Dina, M. T. O’Gorman, M. C. Linhares, W. H. Martin, P. J. Oates, D. A. Tess, G. J. Withbroe, W. J. Zembrowski, J. Med. Chem. 2003, 46, 2283.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXjs12ksLg%3D&md5=dcc18a688428b314c1292d1b59ecf91aCAS | 12773033PubMed |

[27]  V. S. Velezheva, P. J. Brennan, V. Y. Marshakov, D. V. Gusev, I. N. Lisichkina, A. S. Peregudov, L. N. Tchernousova, T. G. Smirnova, S. N. Andreevskaya, A. E. Medvedev, J. Med. Chem. 2004, 47, 3455.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXjvFCgu7g%3D&md5=f19d0a01c35881d0f0cc89af6d2095c6CAS | 15189042PubMed |

[28]  D. Barlocco, G. Cignarella, V. D. Piaz, M. P. Giovannoni, P. G. De Benedetti, F. Fanelli, F. Montesano, E. Poggesi, A. Leonardi, J. Med. Chem. 2001, 44, 2403.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXktlGls7k%3D&md5=f8dc95831db0a417ebe0867c15bb0fafCAS | 11448222PubMed |

[29]  M. F. Brana, M. Cacho, M. L. Garcia, E. P. Mayoral, B. Lopez, B. de Pascual-Teresa, A. Ramos, N. Acero, F. Llinares, D. Munoz-Mingarro, O. Lozach, L. Meijer, J. Med. Chem. 2005, 48, 6843.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXhtVyjt73K&md5=cd4c6d5c6ebe33ed5cc891096889e89aCAS | 16250643PubMed |

[30]  L. A. Black, A. Basha, T. Kolasa, M. E. Kort, H. Q. Liu, C. M. Mccarty, M. V. Patel, J. J. Rohde, M. J. Coghlan, A. O. Stewart, Int. Pat. Appl. WO 0024719 2000.

[31]  S. L. Colletti, J. L. Frie, E. C. Dixon, S. B. Singh, B. K. Choi, G. Scapin, C. E. Fitzgerald, S. Kumar, E. A. Nichols, S. J. O’Keefe, E. A. O’Neill, G. Porter, K. Samuel, D. M. Schmatz, C. D. Schwartz, W. L. Shoop, C. M. Thompson, J. E. Thompson, R. Wang, A. Woods, D. M. Zaller, J. B. Doherty, J. Med. Chem. 2003, 46, 349.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38Xps1Oiur8%3D&md5=fc7c0dba7a0b8a80279d33605cf97eddCAS | 12540232PubMed |

[32]  A. Sacchi, S. Laneri, F. Arena, E. Abignente, M. Gallitelli, M. D’amico, W. Filippelli, F. Rossi, Eur. J. Med. Chem. 1999, 34, 1003.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXotV2qu78%3D&md5=6bfd3ef60a061b263e283374ad4b45e7CAS | 10889324PubMed |

[33]  R. R. Nagawade, V. V. Khanna, S. S. Bhagwat, D. B. Shinde, Eur. J. Med. Chem. 2005, 40, 1325.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXhtF2rurnN&md5=9f633a65f3ba8ea51e6081fb9f3ad3b1CAS | 16126308PubMed |

[34]  C. Liljebris, J. Martinsson, L. Tedenborg, M. Williams, E. Barker, J. E. S. Duffy, A. Nygren, S. James, Bioorg. Med. Chem. Lett. 2002, 10, 3497.

[35]  R. Grey, A. C. Pierce, G. W. Bemis, M. D. Jacobs, C. S. Moody, R. Jajoo, N. Mohal, J. Green, Bioorg. Med. Chem. Lett. 2009, 19, 3019.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXmtVersro%3D&md5=b6d5715ecf396dba86b13e0c917231c6CAS | 19414255PubMed |

[36]  M. Rimaz, H. Mousavi, Turk. J. Chem. 2013, 37, 252.
         | 1:CAS:528:DC%2BC3sXht1Wgt7zF&md5=2566ad7c3c5caea1ceac54babcb63a0dCAS |

[37]  M. Rimaz, H. Rabiei, B. Khalili, R. H. Prager, Aust. J. Chem. 2014, 67, 283.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXitlaqt7c%3D&md5=72fc539d4fa4dc255581bace72c66b27CAS |

[38]  M. Rimaz, P. Pourhossein, B. Khalili, Turk. J. Chem. 2015, 39, 244.
         | Crossref | GoogleScholarGoogle Scholar |

[39]  L. Basolo, E. M. Beccalli, E. Borsini, G. Broggini, Tetrahedron 2009, 65, 3486.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXjsl2htL0%3D&md5=c462cb60d5468f287da14999a3bb1fbaCAS |

[40]  G. Fodor, O. Kovacs, J. Am. Chem. Soc. 1949, 71, 1045.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaH1MXit1Glsg%3D%3D&md5=c26a58089342fb8e2d06acbf95dd95adCAS | 18113541PubMed |

[41]  N. Fresneau, T. Cailly, F. Fabis, J. P. Bouillon, Tetrahedron 2013, 69, 5393.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXnsVylu7g%3D&md5=fe1fbcec13d66816493277a04482d091CAS |

[42]  L. Basolo, E. M. Beccalli, E. Borsini, G. Broggini, Tetrahedron 2009, 65, 3486.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXjsl2htL0%3D&md5=c462cb60d5468f287da14999a3bb1fbaCAS |

[43]  E. Toja, G. Tarzia, D. Barone, F. Luzzani, L. Gallico, J. Med. Chem. 1985, 28, 1314.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2MXkvVWhtLw%3D&md5=8920e38a577de44ee9a87f294486eb3bCAS | 2993620PubMed |

[44]  A. K. Padhy, P. Purohit, M. Bardhan, C. S. Panda, M. P. S. Ishar, Tetrahedron Lett. 2004, 45, 8423.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXotlSmsrg%3D&md5=8c210330c2055701f669f77b289c11eaCAS |

[45]  A. Akbari, Z. Azami-Sardooei, Izv. Him. 2014, 46, 757.