Multicomponent synthesis of 4-aminophthalazin-1(2 H)-ones by palladium-catalyzed isocyanide insertion

Journal of Organic Chemistry

Volumn 78, Issue 13, 2013, Pages 6735-6745

  Vlaar, Tjøstil ^a   Mampuys, Pieter ^b   Helliwell, Madeleine ^c   Maes, Bert U W ^b   Orru, Romano V A ^a   Ruijter, Eelco ^a  

^a AMSTERDAM INSTITUTE FOR MOLECULES   (Netherlands)

^b UNIVERSITY OF ANTWERP   (Belgium)

^c UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CROSS-COUPLINGS; HETEROCYCLIC COMPOUND; ISOCYANIDES; MULTICOMPONENT SYNTHESIS; PALLADIUM-CATALYZED; REGIO-SELECTIVE;

CATALYSIS; ORGANIC COMPOUNDS; SCAFFOLDS;

CYANIDES;

4 AMINOPHTHALAZIN 1(2H) ONE; HYDRAZINE DERIVATIVE; PALLADIUM; PHENYLHYDRAZINE; PHTHALAZINE DERIVATIVE; UNCLASSIFIED DRUG; 4-AMINOPHTHALAZIN-1(2H)-ONE; CYANIDE; ORGANOMETALLIC COMPOUND;

ALKYLATION; ARTICLE; ARYLATION; CATALYSIS; CROSS COUPLING REACTION; DEALKYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME; SOLUTION AND SOLUBILITY; SYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY;

CATALYSIS; CYANIDES; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM; PHTHALAZINES;

EID: 84880018085     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo401131p     Document Type: Article

References (64)

1. Simon, C.; Constantieux, T.; Rodriquez, J. Eur. J. Org. Chem. 2004, 4957-4980
2. Zhu, J.; Bienaymé, H. Multicomponent Reactions; Wiley-VCH: Weinheim, Germany, 2005.
3. Dömling, A. Chem. Rev. 2006, 106, 17-89
4. Ruijter, E.; Scheffelaar, R.; Orru, R. V. A. Angew. Chem., Int. Ed. 2011, 50, 6234-6246
5. Slobbe, P.; Ruijter, E.; Orru, R. V. A. Med. Chem. Commun. 2012, 3, 1189-1218
6. Dömling, A.; Wang, W.; Wang, K. Chem. Rev. 2012, 112, 3083-3135
7. de Graaff, C.; Ruijter, E.; Orru, R. V. A. Chem. Soc. Rev. 2012, 41, 3969-4009
8. Nicolaou, K. C.; Edmonds, D. J.; Bulger, P. G. Angew. Chem., Int. Ed. 2006, 45, 7134-7186
9. Grondal, C.; Jeanty, M.; Enders, D. Nat. Chem. 2010, 2, 167-178
10. Vlaar, T.; Ruijter, E.; Orru, R. V. A. Adv. Synth. Catal. 2011, 353, 809-841
11. Tišler, M.; Stanovnik, B. In Comprehensive Heterocyclic Chemistry I; Katritzky, A. R.; Rees, C. W.; Boulton, A. J.; McKillop, A., Eds.; Elsevier: Amsterdam, 1984; Vol. 3, p 1.
12. Coates, W. J. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V.; Boulton, A. J., Eds.; Elsevier: Amsterdam, 1996; Vol. 6, p 1.
13. Haider, N.; Holzer, W. In Science of Synthesis; Yamamoto, Y., Ed.; Thieme: New York, 2004; Vol. 16, p 315.
14. Maes, B. U. W.; Lemière, G. L. F. In Comprehensive Heterocyclic Chemistry III; Katritzky, A. R.; Ramsden, C. A.; Scriven, E. F. V.; Taylor, R. J. K.; Aitken, A., Eds.; Elsevier: Amsterdam, 2008; Vol. 8, p 1.
15. Prime, M. E.; Courtney, S. M.; Brookfield, F. A.; Marston, R. W.; Walker, V.; Warne, J.; Boyd, A. E.; Kairies, N. A.; von der Saal, W.; Limberg, A.; Georges, G.; Engh, R. A.; Goller, B.; Rueger, P.; Rueth, M. J. Med. Chem. 2011, 54, 312-319
16. Poli, D.; Catarzi, D.; Colotta, V.; Varano, F.; Filacchioni, G.; Daniele, S.; Trincavelli, L.; Martini, C.; Paoletta, S.; Moro, S. J. Med. Chem. 2011, 54, 2102-2113
17. Mevellec, L. A.; Mertens, J. C.; Kennis, L. E. J.; van Dun, J. A. J.; Wouters, W. B. L.; Somers, M. V. F. WO20063147, 2006.
18. Goldstein, D. M.; Rueth, M. US2007219195, 2007.
19. Koza, G.; Keskin, S.; Özer, M. S.; Cengiz, B.; Şahin, E.; Balci, M. Tetrahedron 2013, 69, 395-409
20. Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4442-4489
21. Johansson Seechurn, C. C. C.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Angew. Chem., Int. Ed. 2012, 51, 5062-5085
22. Vlaar, T.; Maes, B. U. W.; Ruijter, E.; Orru, R. V. A. Angew. Chem., Int. Ed. 2013, 10.1002/anie.201300942
23. Lang, S. Chem. Soc. Rev. 2013, 42, 4867-4880
24. Qiu, G.; Ding, Q.; Wu, J. Chem. Soc. Rev. 2013, 42, 5257-5269
25. For a review on carbonylative cross-coupling, see: Brennführer, A.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 4114-4133.
26. Saluste, C. G.; Whitby, R. J.; Furber, M. Angew. Chem., Int. Ed. 2000, 39, 4156-4158
27. Tobisu, M.; Imoto, S.; Ito, S.; Chatani, N. J. Org. Chem. 2010, 75, 4835-4840
28. van Baelen, G.; Kuijer, S.; Rýček, L.; Sergeyev, S.; Janssen, E.; de Kanter, F. J. J.; Maes, B. U. W.; Ruijter, E.; Orru, R. V. A. Chem.-Eur. J. 2011, 17, 15039-15044
29. Zhou, F.; Ding, K.; Cai, Q. Chem.-Eur. J. 2011, 17, 12268-12271
30. Wang, Y.; Wang, H.; Peng, J.; Zhu, Q. Org. Lett. 2011, 13, 4604-4607
31. Miura, T.; Nishida, Y.; Morimoto, M.; Yamauchi, M.; Murakami, M. Org. Lett. 2011, 13, 1429-1431
32. Jiang, H.; Liu, B.; Li, Y.; Wang, A.; Huang, H. Org. Lett. 2011, 13, 1028-1031
33. Boissarie, P. J.; Hamilton, Z. E.; Lang, S.; Murphy, J. A.; Suckling, C. J. Org. Lett. 2011, 13, 6256-6259
34. Tyagi, V.; Khan, S.; Giri, A.; Gauniyal, H. M.; Sridhar, B.; Chauhan, P. M. S. Org. Lett. 2012, 14, 3126-3129
35. Qiu, G.; Liu, G.; Pu, S.; Wu, J. Chem. Commun. 2012, 48, 2903-2905
36. Qiu, G.; He, Y.; Wu, J. Chem. Commun. 2012, 48, 3836-3838
37. Nanjo, T.; Tsukano, C.; Takemoto, Y. Org. Lett. 2012, 14, 4270-4173
38. Liu, B.; Li, Y.; Jiang, H.; Yin, M.; Huang, H. Adv. Synth. Catal. 2012, 354, 2288-2300
39. Li, Y.; Zhao, J.; Chen, H.; Liu, B.; Jiang, H. Chem. Commun. 2012, 48, 3545-3547
40. Xu, S.; Huang, X.; Hong, X.; Xu, B. Org. Lett. 2012, 14, 4614-4617
41. Wang, Y.; Zhu, Q. Adv. Synth. Catal. 2012, 354, 1902-1908
42. Peng, J.; Zhao, J.; Hu, Z.; Liang, D.; Huang, J.; Zhu, Q. Org. Lett. 2012, 14, 4966-4969
43. Peng, J.; Liu, L.; Hu, Z.; Huang, J.; Zhu, G. Chem. Commun. 2012, 48, 3772-3774
44. Hu, Z.; Liang, D.; Zhao, J.; Huang, J.; Zhu, Q. Chem. Commun. 2012, 48, 7371-7373
45. Fei, X.-D.; Ge, Z.-Y.; Tang, T.; Zhu, Y.-M.; Ji, S.-J. J. Org. Chem. 2012, 77, 10321-10328
46. Liu, B.; Li, Y.; Yin, M.; Wu, W.; Jiang, H. Chem. Commun. 2012, 48, 11446-11448
47. Vlaar, T.; Cioc, R. C.; Mampuys, P.; Maes, B. U. W.; Orru, R. V. A.; Ruijter, E. Angew. Chem., Int. Ed. 2012, 51, 13058-13061
48. Tang, T.; Fei, X.-D.; Ge, Z.-Y.; Chen, Z.; Zhu, Y.-M.; Ji, S. J. J. Org. Chem. 2013, 78, 3170-3175
49. Geden, J. V.; Pancholi, A. K.; Shipman, M. J. Org. Chem. 2013, 78, 4158-4164
50. Vlaar, T.; Ruijter, E.; Znabet, A.; Janssen, E.; de Kanter, F. J. J.; Maes, B. U. W.; Orru, R. V. A. Org. Lett. 2011, 13, 6496-6499
51. For a related Pd-catalyzed carbonylative approach towards 4-unsubstituted phthalazinones from 2-bromobenzaldehydes and hydrazines, see: Wu, X.-F.; Neumann, H.; Neumann, S.; Beller, M. Chem.-Eur. J. 2012, 18, 8596-8599
52. Hostyn, S.; Maes, B. U. W.; van Baelen, G.; Gulevskaya, A.; Meyers, C.; Smits, K. Tetrahedron 2006, 62, 4676-4684
53. Kappe, C. O.; Pieber, B.; Dallinger, D. Angew. Chem., Int. Ed. 2013, 52, 1088-1094
54. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320-330
55. Procopiou, P. A.; Browning, C.; Gore, P. M.; Lynn, S. M.; Richards, S. A.; Slack, R. J.; Sollis, S. L. Bioorg. Med. Chem. 2012, 20, 6097-6108
56. Guchhait, S. K.; Madaan, C. Org. Biomol. Chem. 2010, 8, 3631-3634
57. Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727-7729
58. Bienaymé, H.; Bouzid, K. Angew. Chem., Int. Ed. 1998, 37, 2234-2237
59. Blackburn, C. Tetrahedron Lett. 1998, 39, 5469-5472
60. Blackburn, C.; Guan, B.; Fleming, P.; Shiosaki, K.; Tsai, S. Tetrahedron Lett. 1998, 39, 3635-3638
61. Groebke, K.; Weber, L.; Mehlin, F. Synlett 1998, 1998, 661-663
62. Watanabe, N.; Adachi, H.; Takase, Y.; Ozaki, H.; Matsukura, M.; Miyazaki, K.; Ishibashi, K.; Ishihara, H.; Kodama, K.; Nishino, M.; Kakiki, M.; Kabasawa, Y. J. Med. Chem. 2000, 43, 2523-2529
63. Duncton, M. A. J.; Piatnitski Chekler, E. L.; Katoch-Rouse, R.; Sherman, D.; Wong, W. C.; Smith, L. M., II; Kawakami, J. K.; Kiselyov, A. S.; Milligan, D. L.; Balagtas, C.; Hadari, Y. R.; Wang, Y.; Patel, S. N.; Rolster, R. L.; Tonra, J. R.; Surguladze, D.; Mitelman, S.; Kussie, P.; Bohlen, P.; Doody, J. F. Bioorg. Med. Chem. 2009, 17, 731-740
64. Mongin, F.; Desponds, O.; Schlosser, M. Tetrahedron Lett. 1996, 37, 2767-2770