Synthesis of tetrahydrophthalazine and phthalamide (phthalimide) derivatives via palladium-catalysed carbonylation of iodoarenes

Tetrahedron

Volumn 67, Issue 47, 2011, Pages 9122-9128

  Marosvölgyi Haskó, Diána ^a   Petz, Andrea ^a   Takács, Attila ^a   Kollár, László ^a  

^a UNIVERSITY OF PÉCS   (Hungary)

Author keywords

Amino acid; Aminocarbonylation; Carbon monoxide; Hydrazinocarbonylation; Palladium; Tetrahydrophthalazine

Indexed keywords

1,2 DIIODOBENZENE; 1,2,3,4 TETRAHYDROPHTHALAZIN 1 ONE DERIVATIVE; 1,2,3,4 TETRAHYDROPHTHALAZIN 1,4 DIONE DERIVATIVE; 2 IODOBENZYL BROMIDE; AMIDE; BENZENE DERIVATIVE; CARBON MONOXIDE; HYDRAZINE DERIVATIVE; IODOARENES; NUCLEOPHILE; PALLADIUM; PHTHALAZINE DERIVATIVE; PHTHALIMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CARBONYLATION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 80054772225     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.09.095     Document Type: Article

References (28)

1. T. Kline, L. Mueller, E. SieberMcMaster, W.F. Lau, and C.A. Meyers Int. J. Pept. Protein Res. 47 1996 142 147
2. I. Maeba, T. Ishikawa, and H. Furukawa Carbohydr. Res. 140 1985 332 335
3. K. Mogilaiah, J.U. Rani, and H.S. Babu Indian J. Chem., Sect. B 46 2007 1361 1363
4. B.I. Buzykin, A.P. Stolyarov, and N.N. Bystrykh Tetrahedron Lett. 21 1980 209 210
5. R. Grigg, V. Sridharan, M. Shah, S. Mutton, C. Kilner, D. MacPherson, and P. Milner J. Org. Chem. 73 2008 8352 8356
6. L. Kollár, Z. Szarka, J. Horváth, and Z. Tuba Tetrahedron Lett. 38 1997 4467 4468
7. R. Skoda-Földes, Z. Szarka, L. Kollár, Z. Dinya, J. Horváth, and Z. Tuba J. Org. Chem. 64 1999 2134 2136
8. Z. Szarka, R. Skoda-Földes, J. Horváth, Z. Tuba, and L. Kollár Steroids 67 2002 581 586
9. E. Licandro, and D. Perdicchia Eur. J. Org. Chem. 2004 665 675
10. R.J. Perry, and S.R. Turner J. Org. Chem. 56 1991 6573 6579
11. L.S. Liebeskind, and M.S. South J. Org. Chem. 45 1980 5426 5429
12. H. Cao, and H. Alper Org. Lett. 12 2010 4126 4129
13. M.T. Baumgartner, L.B. Jimenez, A.B. Pierini, and R.A. Rossi J. Chem. Soc., Perkin Trans. 2 2002 1092 1097
14. L.S. Zhou, K. Nakajima, K. Kanno, and T. Tzakahashi Tetrahedron Lett. 50 2009 2722 2726
15. M. Janka, W. He, A.J. Frontier, and R. Eisenberg J. Am. Chem. Soc. 126 2004 6864 6865
16. M. Janka, W. He, A.J. Frontier, C. Flaschenriem, and R. Eisenberg Tetrahedron 61 2005 6193 6206
17. J. Terao, A. Wadahama, T. Fujihara, and Y. Tsuji Chem. Lett. 39 2010 518 519
18. H. Nuske, S. Brase, S.I. Kozhuskov, M. Noltemeyer, M. Es-Sayed, and A. de Mejiere Chem. - Eur. J. 8 2002 2350 2369
19. F.T. Luo, A. Jeevanandam, and M.K. Basu Tetrahedron Lett. 39 1998 7939 7942
20. D.J. Sinclair, and M.S. Sherburn J. Org. Chem. 70 2005 3730 3733
21. A. Schoenberg, and R.F. Heck J. Org. Chem. 39 1974 3327 3331
22. C. Amatore, A. Jutand, and M.A. M'Barki Organometallics 11 1992 3009 3013
23. C. Amatore, A. Jutand, F. Khalil, M.A. M'Barki, and L. Mottier Organometallics 12 1993 3168 3178
24. C. Amatore, E. Carre, A. Jutand, M.A. M'Barki, and G. Meyer Organometallics 14 1995 5605 5614
25. Z. Csákai, R. Skoda-Földes, and L. Kollár Inorg. Chim. Acta 286 1999 93 97
26. A.N. Kost, K. Grabliauskas, V.G. Vinokurov, and A.M. Zhakun J. Prakt. Chem. 312 1970 542 544
27. J. Nematollahi J. Heterocyclic Chem. 9 1972 963 965
28. L. Smith, and O.H. Emerson J. Am. Chem. Soc. 67 1945 1862