Synthesis of 2-aryl-1,2-dihydrophthalazines via reaction of 2-(bromomethyl)benzaldehydes with arylhydrazines

Journal of Organic Chemistry

Volumn 78, Issue 3, 2013, Pages 1045-1053

  Aljaar, Nayyef ^a   Conrad, Jürgen ^a   Beifuss, Uwe ^a  

^a UNIVERSITY OF HOHENHEIM   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLHYDRAZINES; INTERMOLECULAR CONDENSATION; NUCLEOPHILIC SUBSTITUTIONS;

CHEMISTRY; ORGANIC COMPOUNDS;

ALDEHYDES;

2 (2,4 DIMETHYLPHENYL) 1,2 DIHYDROPHTHALAZINE; 2 (3 CHLOROPHENYL) 1,2 DIHYDROPHTHALAZINE; 2 (3 FLUOROPHENYL) 1,2 DIHYDROPHTHALAZINE; 2 (3 METHYLPHENYL) 1,2 DIHYDROPHTHALAZINE; 2 (3,4 DIMETHYLPHENYL) 1,2 DIHYDROPHTHALAZINE; 2 (4 CYANOPHENYL) 1,2 DIHYDROPHTHALAZINE; 2 (4 ISOPROPYLPHENYL) 1,2 DIHYDROPHTHALAZINE; 2 (4 METHOXYPHENYL) 1,2 DIHYDROPHTHALAZINE; 2 (4 METHYLPHENYL) 1,2 DIHYDROPHTHALAZINE; 2 (BROMOMETHYL) 3 CHLOROBENZALDEHYDE; 2 (BROMOMETHYL) 6 CHLOROBENZALDEHYDE; 2 (BROMOMETHYL)BENZALDEHYDE; 2 PHENYL 1,2 DIHYDROPHTHALAZINE; 4 BROMO 2 (BROMOMETHYL)BENZALDEHYDE; 5 CHLORO 2 PHENYL 1,2 DIHYDROPHTHALAZINE; 7 CHLORO 2 PHENYL 1,2 DIHYDROPHTHALAZINE; 8 CHLORO 2 PHENYL 1,2 DIHYDROPHTHALAZINE; BENZALDEHYDE DERIVATIVE; HYDRAZINE DERIVATIVE; PHENYLHYDRAZINE; PHTHALAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; POLYMERIZATION; SUBSTITUTION REACTION; SYNTHESIS;

BENZALDEHYDES; CATALYSIS; MOLECULAR STRUCTURE; PHTHALAZINES;

EID: 84873402816     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo302491x     Document Type: Article

References (41)

1. El-Hashash, M. A.; El-Kady, A. Y.; Taha, M. A.; El-Shamy, I. E. Chin. J. Chem. 2012, 30, 616
2. Awadallah, F. M.; El-Eraky, W. I.; Saleh, D. O. Eur. J. Med. Chem. 2012, 52, 14
3. Sriram, D.; Yogeeswari, P.; Senthilkumar, P.; Sangaraju, D.; Nelli, R.; Banerjee, D.; Bhat, P.; Manjashetty, T. H. Chem. Biol. Drug Des. 2010, 75, 381
4. Abd alla, M. S. M.; Hegab, M. I.; Abo Taleb, N. A.; Hasabelnaby, S. M.; Goudah, A. Eur. J. Med. Chem. 2010, 45, 1267
5. Zhang, L.; Guan, L.-P.; Sun, X.-Y.; Wei, C.-X.; Chai, K.-Y.; Quan, Z.-S. Chem. Biol. Drug Des. 2009, 73, 313
6. Ryu, C.-K.; Park, R.-E.; Ma, M.-Y.; Nho, J.-H. Bioorg. Med. Chem. Lett. 2007, 17, 2577
7. del Olmo, E.; Barboza, B.; Ybarra, M. I.; López-Pérez, J. L.; Carrón, R.; Sevilla, M. A.; Boselli, C.; Feliciano, A. S. Bioorg. Med. Chem. Lett. 2006, 16, 2786
8. Shetgiri, N. P.; Nayak, B. K. Ind. J. Chem., Sect. B 2005, 44, 1267
9. Demirayak, S.; Karaburun, A. C.; Beis, R. Eur. J. Med. Chem. 2004, 39, 1089
10. Kim, J. S.; Lee, H.-J.; Suh, M.-E.; Choo, H.-Y. P.; Lee, S. K.; Park, H. J.; Kim, C.; Park, S. W.; Lee, C.-O. Bioorg. Med. Chem. 2004, 12, 3683
11. Sivakumar, R.; Gnanasam, S. K.; Ramachandran, S.; Leonard, J. T. Eur. J. Med. Chem. 2002, 37, 793
12. Van der Mey, M.; Boss, H.; Couwenberg, D.; Hatzelmann, A.; Sterk, G. J.; Goubitz, K.; Schenk, H.; Timmerman, H. J. Med. Chem. 2002, 45, 2526
13. Madhavan, G. R.; Chakrabarti, R.; Kumar, S. K. B.; Misra, P.; Mamidi, R. N. V. S.; Balraju, V.; Kasiram, K.; Babu, R. K.; Suresh, J.; Lohray, B. B.; Lohray, V. B.; Iqbal, J.; Rajagopalan, R. Eur. J. Med. Chem. 2001, 36, 627
14. Kornet, M. J.; Shackleford, G. J. Heterocycl. Chem. 1999, 36, 1095
15. Watanabe, N.; Kabasawa, Y.; Takase, Y.; Matsukura, M.; Miyazaki, K.; Ishihara, H.; Kodama, K.; Adachi, H. J. Med. Chem. 1998, 41, 3367
16. Brown, D. J. Cinnolines and Phthalazines. In Chemistry of Heterocyclic Compounds; Taylor, E. C.; Wipf, P., Eds.; John Wiley & Sons: Hoboken, NJ, 2005; Vol. 64, p 109.
17. Castle, R. N. Condensed Pyridazines including Cinnolines and Phthalazines. In Chemistry of Heterocyclic Compounds; Weissberger, A.; Taylor, E. C., Eds.; John Wiley & Sons: Toronto, 1973; Vol. 27, p 325.
18. Clark, C.; Ednie, L. M.; Lin, G.; Smith, K.; Kosowska-Shick, K.; McGhee, P.; Dewasse, B.; Beachel, L.; Caspers, P.; Gaucher, B.; Mert, G.; Shapiro, S.; Appelbaum, P. C. Antimicrob. Agents Chemother. 2009, 53, 1353
19. Caspers, P.; Bury, L.; Gaucher, B.; Heim, J.; Shapiro, S.; Siegrist, S.; Schmitt-Hoffmann, A.; Thenoz, L.; Urwyler, H. Antimicrob. Agents Chemother. 2009, 53, 3620
20. Bourne, C. R.; Barrow, E. W.; Bunce, R. A.; Bourne, P. C.; Berlin, K. D.; Barrow, W. W. Antimicrob. Agents Chemother. 2010, 54, 3825
21. Bourne, C. R.; Bunce, R. A.; Bourne, P. C.; Berlin, K. D.; Barrow, E. W.; Barrow, W. W. Antimicrob. Agents Chemother. 2009, 53, 3065
22. Pelletier, J. C.; Hesson, D. P.; Jones, K. A.; Costa, A.-M. J. Med. Chem. 1996, 39, 343
23. Alper, H. J. Org. Chem. 1972, 37, 3972
24. Lukács, G.; Simig, G. J. Heterocycl. Chem. 2002, 39, 989
25. Nguyen, M. T. J. Org. Chem. 1990, 55, 6177
26. Smith, R. F.; Otremba, E. D. J. Org. Chem. 1962, 27, 879
27. Hirsch, A.; Orphanos, D. G. J. Heterocycl. Chem. 1966, 3, 38
28. Butler, R. N.; Gillan, A. M.; Lysaght, F. A.; McArdle, P.; Cunningham, D. J. Chem. Soc., Perkin Trans. 1990, 1, 555
29. Ju, Y.; Varma, R. S. J. Org. Chem. 2006, 71, 135
30. Ju, Y.; Varma, R. S. Tetrahedron Lett. 2005, 46, 6011
31. Li, G.; Ding, Z.; Xu, B. Org. Lett. 2012, 14, 5338
32. Sudheendran, K.; Malakar, C. C.; Conrad, J.; Beifuss, U. J. Org. Chem. 2012, 77, 10194
33. Aljaar, N.; Malakar, C. C.; Conrad, J.; Strobel, S.; Schleid, T.; Beifuss, U. J. Org. Chem. 2012, 77, 7793
34. Malakar, C. C.; Baskakova, A.; Conrad, J.; Beifuss, U. Chem.-Eur. J. 2012, 18, 8882
35. Malakar, C. C.; Sudheendran, K.; Imrich, H.-G.; Mika, S.; Beifuss, U. Org. Biomol. Chem. 2012, 10, 3899
36. Malakar, C. C.; Schmidt, D.; Conrad, J.; Beifuss, U. Org. Lett. 2011, 8, 1972
37. Shah, J. R.; Mosier, P. D.; Peddi, S.; Roth, B. L.; Westkaemper, R. B. Bioorg. Med. Chem. Lett. 2010, 20, 935
38. Zhang, X.-X.; Lippard, S. J. J. Org. Chem. 2000, 65, 5298
39. Bookser, B. C.; Bruice, T. C. J. Am. Chem. Soc. 1991, 113, 4202
40. 3N according to the procedure of: Markwalder, J. A.; Arnone, M. R.; Benfield, P. A.; Boisclair, M.; Burton, C. R.; Chang, C.-H.; Cox, S. S.; Czerniak, P. M.; Dean, C. L.; Doleniak, D.; Grafstrom, R.; Harrison, B. A.; Kaltenbach, R. F.; Nugiel, D. A.; Rossi, K. A.; Sherk, S. R.; Sisk, L. M.; Stouten, P.; Trainor, G. L.; W orland, P.; Seitz, S. P. J. Med. Chem. 2004, 47, 5894
41. Devadas, B.; Hartmann, S. J.; Heier, R. F.; Jerome, K. D.; Kolodziej, S. A.; Mathias, J. P.; Norton, M. B.; Promo, M. A.; Rucker, P. V.; Selness, S. R. U.S. Patent 0,270,350, Oct 29, 2009.