First synthesis of 4,5-dihydro-3(2H)-pyridazinones via Zn-mediated hydrohydrazination

Tetrahedron Letters

Volumn 49, Issue 31, 2008, Pages 4607-4609

  Alex, Karolin ^a   Tillack, Annegret ^a   Schwarz, Nicolle ^a   Beller, Matthias ^a  

^a LEIBNIZ INSTITUT FÜR KATALYSE E V AN DER UNIVERSITÄT ROSTOCK   (Germany)

Author keywords

Hydrazine; Hydroamination; Intermolecular; Pentynoic acid; Pyridazinone; Zinc

Indexed keywords

4 PENTYNOIC ACID; 4,5 DIHYDRO 3(2H) PYRIDAZINONE DERIVATIVE; ALKYNE DERIVATIVE; HYDRAZINE DERIVATIVE; ZINC; ZINC CHLORIDE;

AMIDATION; AMINATION; ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS;

EID: 45049083614     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.05.084     Document Type: Article

References (47)

1. Mitchinson A., Blackaby W.P., Bourrain S., Carling R.W., and Lewis R.T. Tetrahedron Lett. 47 (2006) 2257-2260
2. Review. Lee S.-G., Kim J.-J., Kim H.-K., Kweon D.-H., Kang Y.-J., Cho S.-D., Kim S.-K., and Yoon Y.-J. Curr. Org. Chem. 8 (2004) 1463-1480
3. Byth K.F., Cooper N., Culshaw J.D., Heaton D.W., Oajes S.F., Minshull C.A., Norman R.A., Pauptit R.A., Tucker J.A., Breed J., Pannifer A., Roswell S., Slanway J.J., Valentine A.L., and Thomas A.P. Bioorg. Med. Chem. Lett. 14 (2004) 2249-2252
4. Velentza A.V., Wainwright M.S., Zadadzki M., Mirzoeva S., Schumacher M., Haiech J., Focia P.J., Egli M., and Waterson D.M. Bioorg. Med. Chem. Lett. 13 (2003) 3465-3470
5. Contreras J.M., Parrot I., Sippl W., Rival Y.M., and Wermuth C.G. J. Med. Chem. 44 (2001) 2707-2718
6. Katritzky A.R., Pleynet D.P.M., Yang B., and Yao J. Synthesis (1998) 1627-1630 and references therein
7. Review. Matyus P. J. Heterocycl. Chem. 35 (1998) 1075-1089
8. Coates W.J. Pyridazines and Their Benzo Derivatives. In: Katritzky A.R., Rees C.W., and Scriven E.F.V. (Eds). Comprehensive Heterocyclic Chemistry II Vol. 6 (1996), Pergamon Press, Oxford 191
9. Estevez I., Ravina E., and Sotelo E. J. Heterocycl. Chem. 35 (1998) 1421-1428 and references therein
10. Sircar I., Duell B.L., Bobowski G., Bristol J.A., and Evans D.B. J. Med. Chem. 28 (1985) 1405-1413
11. Bristol J.A. J. Med. Chem. 27 (1984) 1099-1101
12. Campos K.R., Woo J.C.S., Lee S., and Tillyer R.D. Org. Lett. 6 (2004) 79-82
13. Gouault N., Cupif J.F., Picard S., Lecat A., and David M. J. Pharm. Pharmacol. 53 (2001) 981-985
14. Ege S.N., Carter M.L.C., Ortwine D.F., Chou S.-S.P., and Richman J.F. J. Chem. Soc., Perkin Trans. 1 (1977) 1252-1257
15. Wamhoff H., and Korte F. Liebigs Ann. Chem. 724 (1969) 217-220
16. Stevens F.J., Griffin T.D., and Fields T.L. J. Am. Chem. Soc. 77 (1955) 42-44
17. Fischer E. Liebigs Ann. Chem. 236 (1886) 126-151
18. Recent selected examples:. Murphy D.E., Dragovich P.S., Ayida B.K., Bertolini T.M., Li L.-S., Ruebsam F., Stankovic N.S., Sun Z., Zhao J., and Zhou Y. Tetrahedron Lett. 49 (2008) 811-815
19. Mohamed N.R., El-Saidi M.M.T., Ali Y.M., and Elnagdi M.H. J. Heterocycl. Chem. 44 (2007) 1333-1337
20. de Araujo-Junior J.X., Schmitt M., Antheaume C., and Bourguignon J.-J. Tetrahedron Lett. 48 (2007) 7817-7820
21. Helm M.D., Plant A., and Harrity J.P.A. Org. Biomol. Chem. 4 (2006) 4278-4280
22. Alex K., Tillack A., Schwarz N., and Beller M. ChemSusChem 1 (2008) 333-338
23. Tillack A., Khedkar V., Jiao H., and Beller M. Eur. J. Org. Chem. (2005) 5001-5012
24. Tillack A., Khedkar V., and Beller M. Tetrahedron Lett. 45 (2004) 8875-8878
25. Khedkar V., Tillack A., and Beller M. Org. Lett. 5 (2003) 4767-4770
26. Tillack A., Garcia Castro I., Hartung C.G., and Beller M. Angew. Chem. 114 (2002) 2646-2648
27. Angew. Chem., Int. Ed. 41 (2002) 2541-2543
28. Selected recent reviews on hydroaminations of alkynes:. Severin R., and Doye S. Chem. Soc. Rev. 36 (2007) 1407-1420
29. Lee A.V., and Schafer L.L. Eur. J. Inorg. Chem. (2007) 2243-2255
30. Alonso F., Beletskaya I.P., and Yus M. Chem. Rev. 104 (2004) 3079-3159
31. Alex K., Schwarz N., Khedkar V., Sayyed I.A., Tillack A., Michalik D., Holenz J., Diaz J.L., and Beller M. Org. Biomol. Chem. 6 (2008) 1802-1807
32. Sayyed I.A., Alex K., Tillack A., Schwarz N., Spannenberg A., Michalik D., and Beller M. Tetrahedron 64 (2008) 4590-4595
33. Schwarz N., Alex K., Sayyed I.A., Khedkar V., Tillack A., and Beller M. Synlett (2007) 1091-1095
34. Sayyed I.A., Alex K., Tillack A., Schwarz N., Michalik D., and Beller M. Eur. J. Org. Chem. (2007) 4525-4528
35. Khedkar V., Tillack A., Michalik D., and Beller M. Tetrahedron 61 (2005) 7622-7631
36. Tillack A., Jiao H., Garcia Castro I., Hartung C.G., and Beller M. Chem. Eur. J. 10 (2004) 2409-2420
37. Khedkar V., Tillack A., Michalik M., and Beller M. Tetrahedron Lett. 45 (2004) 3123-3126
38. Banerjee S., Barnea E., and Odom A.L. Organometallics 27 (2008) 1005-1014
39. Ackermann L., and Born R. Tetrahedron Lett. 45 (2004) 9541-9544
40. Cao C., Shi Y., and Odom A.L. Org. Lett. 4 (2002) 2853-2856
41. Walsh P.T., Carney M.J., and Bergman R.G. J. Am. Chem. Soc. 113 (1991) 6343-6345
42. Alex, K.; Tillack, A.; Schwarz, N.; Beller, M. Org. Lett., in press.
43. Alex K., Tillack A., Schwarz N., and Beller M. Angew. Chem. 120 (2008) 2337-2340
44. Angew. Chem., Int. Ed. 47 (2008) 2304-2307
45. For a recent review on Markovnikov and anti-Markovnikov functionalization of olefins and alkynes, see:. Seayad J., Tillack A., Jiao H., and Beller M. Angew. Chem. 116 (2004) 3448-3479
46. Angew. Chem., Int. Ed. 43 (2004) 3368-3398
47. For recent review in Friedel-Crafts acylation reaction, see:. Sartori G., and Maggi R. Chem. Rev. 106 (2006) 1077-1104