Efficient access to (1H)-isoindolin-1-one-3-carboxylic acid derivatives by orthopalladation and carbonylation of methyl arylglycinate substrates

Tetrahedron

Volumn 67, Issue 23, 2011, Pages 4185-4191

  Nieto, Sonia ^a   Sayago, Francisco J ^a   Laborda, Pedro ^a   Soler, Tatiana ^b   Cativiela, Carlos ^a   Urriolabeitia, Esteban P ^a  

^a UNIVERSITY OF ZARAGOZA   (Spain)

^b San Vicente de Raspeig   (Spain)

Author keywords

Carbonylation; Hydrogenation; Isoindolones; Palladium; Phenylglycine

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; GLYCINE DERIVATIVE; ISOINDOLE DERIVATIVE; LEAD; METHYL 4 BROMO(1H)ISOINDOLIN 1 ONE 3 CARBOXYLATE; METHYL 5 BROMO(1H)ISOINDOLIN 1 ONE 3 CARBOXYLATE; METHYL 6 BROMO(1H)ISOINDOLIN 1 ONE 3 CARBOXYLATE; METHYL 6 METHOXY(1H)ISOINDOLIN 1 ONE 3 CARBOXYLATE; METHYL N(TERT BUTOXYCARBONYL)OCTAHYDROISOINDOL 1 CARBOXYLATE; METHYL N(TERT BUTOXYCARBONYL)OCTAHYDROISOINDOL 1 ONE 3 CARBOXYLATE; METHYL OCTAHYDROISOINDOL 1 ONE 3 CARBOXYLATE; METHYL(2 BROMOPHENYL)GLYCINATE; METHYL(3 BROMOPHENYL)GLYCINATE; METHYL(4 BROMOPHENYL)GLYCINATE; METHYL(4 METHOXYPHENYL)GLYCINATE; UNCLASSIFIED DRUG;

ARTICLE; CARBONYLATION; CHEMICAL MODIFICATION; ELECTRON TRANSPORT; HYDROGENATION; ORTHOPALLADATION; PRIORITY JOURNAL; STEREOCHEMISTRY; STRECKER SYNTHESIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 79956070576     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.04.064     Document Type: Article

References (71)

1. J.H. Lee, S.R. Byeon, Y.S. Kim, S.J. Lim, S.J. Oh, H.C. Moon, K.H. Yoo, B.Y. Chung, and D.J. Kim Bioorg. Med. Chem. Lett. 18 2008 5701
2. S. Lee, C. Shinji, K. Ogura, M. Shimizu, S. Maeda, M. Sato, M. Yoshida, Y. Hashimoto, and H. Miyachi Bioorg. Med. Chem. Lett. 17 2007 4895
3. T. Lübbers, P. Angehrn, H. Gmünderb, and S. Herzig Bioorg. Med. Chem. Lett. 17 2007 4708
4. D. Hamprecht, F. Micheli, G. Tedesco, A. Checchia, D. Donati, M. Petrone, S. Terreni, and M. Wood Bioorg. Med. Chem. Lett. 17 2007 428
5. J. Guillaumel, S. Léonce, A. Pierré, P. Renard, B. Pfeiffer, P.B. Arimondo, and C. Monneret Eur. J. Med. Chem. 41 2006 379
6. T. Honma, K. Hayashi, T. Aoyama, N. Hashimoto, T. Machida, K. Fukasawa, T. Iwama, C. Ikeura, M. Ikuta, I. Suzuki-Takahashi, Y. Iwasawa, T. Hayama, S. Nishimura, and H. Morishima J. Med. Chem. 44 2001 4615
7. J.K. Kim, Y.H. Kim, H.T. Nam, B.T. Kim, and J.-N. Heo Org. Lett. 10 2008 3543
8. H. Wehlan, E. Jezek, N. Lebrasseur, G. Pavé, E. Roulland, A.J.P. White, J.N. Burrows, and A.G.M. Barrett J. Org. Chem. 71 2006 8151
9. D.L. Comins, S. Schilling, and Y. Zhang Org. Lett. 7 2005 95
10. U.C. Yoon, Y.X. Jin, S.W. Oh, C.H. Park, J.H. Park, C.F. Campana, X. Cai, E.N. Duesler, and P.S. Mariano J. Am. Chem. Soc. 125 2003 10664
11. J.T. Link, S. Raghavan, and S.J. Danishefsky J. Am. Chem. Soc. 117 1995 552
12. M. Lamblin, A. Couture, E. Deniau, and P. Grandclaudon Tetrahedron: Asymmetry 19 2008 111
13. For the antihypertensive activity see: J.-M. Ferland, C.A. Demerson, and L.G. Humber Can. J. Chem. 63 1985 361 For the antipsychotic activity see:
14. Z.-P. Zhuang, M.-P. Kung, M. Mu, and H.F. Kung J. Med. Chem. 41 1998 157
15. M. Linden, D. Hadler, and S. Hofmann Hum. Psychopharmacol. 12 1997 445
16. M.H. Norman, D.J. Minick, and G.C. Rigdon J. Med. Chem. 39 1996 149 For the antiinflammatory activity see:
17. S. Li, X. Wang, H. Guo, and L. Chen Yiyao Gongye 16 1985 543
18. Chem. Abstr. 105 1986 6378 For the anaesthesic activity see:
19. Laboratori Baldacci, S.P.A. Japanese Patent 5,946,268, 1984;
20. Chem. Abstr. 101 1984 54922 For the antiulcer activity see:
21. Lippmann, W. U.S. Patent 4,267,189, 1981;
22. Chem. Abstr. 95 1981 61988 For the antiviral activity see:
23. E. De Clercq J. Med. Chem. 38 1995 2491
24. I. Pendrak, S. Barney, R. Wittrock, D.M. Lambert, and W.D. Kingsbury J. Org. Chem. 59 1994 2623 For the antileukemic activity see:
25. E.C. Taylor, P. Zhou, L.D. Jennings, Z. Mao, B. Hu, and J.-G. Jun Tetrahedron Lett. 38 1997 521
26. Arvidsson, P.; Besidski, Y.; Csjernyik, G.; Lange, T.; Macsári, I.; Nilsson, L. WO 2009/145718 A1;
27. Chem. Abstr. 152 2009 12153
28. Björe, A.; Boström, J.; Davidsson, O.; Emtenäs, H.; Gran, U.; Iliefski, T.; Kajanus, J.; Olsson, R.; Sandberg, L.; Strandlund, G.; Sundell. J.; Kuan, Z.-Q. WO 2008/008022 A1;
29. Chem. Abstr. 148 2008 168577
30. M. Othman, P. Pigeon, and B. Decroix Tetrahedron 54 1998 8737
31. M. Othman, and B. Decroix Synth. Commun. 26 1996 2803
32. C. Banzatti, N. Carfagna, R. Commisso, F. Heidempergher, L. Pegrassi, and P. Melloni J. Med. Chem. 31 1988 1466
33. E. Valencia, A. Patra, A.J. Freyer, M. Shamma, and V. Fajardo Tetrahedron Lett. 25 1984 3163
34. R. Ben-Othman, M. Othman, K. Ciamala, M. Knorr, C. Strohmann, and B. Decroix Tetrahedron 65 2009 4846
35. R. Ben-Othman, M. Othman, S. Coste, and B. Decroix Tetrahedron 64 2008 559
36. A. El Nemr Tetrahedron 56 2000 8579
37. G. Legler Adv. Carbohydr. Chem. Biochem. 48 1990 319
38. G.K. Ostrander, N.K. Scribner, and L.R. Rohrschneider Cancer Res. 48 1988 1091
39. A.D. Elbein Annu. Rev. Biochem. 56 1987 497
40. T. Kametani, H. Suguhara, and K. Kanno Chem. Pharm. Bull. 15 1967 1916
41. J.A. Lowe, and F.E. Ewing J. Heterocycl. Chem. 24 1987 877
42. A. Couture, E. Deniau, D. Ionescu, and P. Grandclaudon Tetrahedron Lett. 39 1998 2319
43. J.M. Thompson, and R.F. Heck J. Org. Chem. 40 1975 2667
44. L. Kollar Modern Carbonylation Methods 2006 Wiley-VCH, Weinhein Germany
45. A. Brennführer, H. Neumann, and M. Beller Angew. Chem., Int. Ed. 48 2009 4114
46. Selected examples of catalytic processes: J.C. Anderson, A. Flaherty, and M.E. Swarbrick J. Org. Chem. 65 2000 9152
47. R. Grigg, L. Zhang, S. Collard, and A. Keep Tetrahedron Lett. 44 2003 6979
48. K. Orito, A. Horibata, T. Nakamura, H. Ushito, H. Nagasaki, M. Yuguchi, S. Yamashita, and M. Tokuda J. Am. Chem. Soc. 126 2004 14342
49. K. Orito, M. Miyazawa, T. Nakamura, A. Horibata, H. Ushito, H. Nagasaki, M. Yuguchi, S. Yamashita, T. Yamazaki, and M. Tokuda J. Org. Chem. 71 2006 5951
50. Y. Wada, H. Nagasaki, M. Tokuda, and K. Orito J. Org. Chem. 72 2007 2008
51. W. Ren, and M. Yamane J. Org. Chem. 74 2009 8332
52. C.S. Cho, and W.X. Ren Tetrahedron Lett. 50 2009 2097
53. B. López, A. Rodríguez, D. Santos, J. Albert, X. Ariza, J. García, and J. Granell Chem. Commun. 2011 1054 Selected examples of stoichiometric processes:
54. J. Dupont, M. Pfeffer, J.C. Daran, and Y. Jeannin Organometallics 6 1987 899
55. J. Vicente, I. Saura-Llamas, J.A. García-López, B. Calmuschi-Cula, and D. Bautista Organometallics 26 2007 2768
56. J. Vicente, I. Saura-Llamas, J.A. García-López, and D. Bautista Organometallics 28 2009 448
57. S. Nieto, P. Arnau, E. Serrano, R. Navarro, T. Soler, C. Cativiela, and E.P. Urriolabeitia Inorg. Chem. 48 2009 11963
58. For a recent example see: M. Van der Linden, J. Borsboom, F. Kaspersen, and G. Kemperman Eur. J. Org. Chem. 2008 2989
59. Y. Fuchita, K. Yoshinaga, Y. Ikeda, and J. Kinoshita-Kawashima J. Chem. Soc., Dalton Trans. 1997 2495
60. A.J. Deeming, I.P. Rothwell, M.B. Hursthouse, and L. New J. Chem. Soc., Dalton Trans. 1978 1490
61. Guzzo, P. R.; Hamby, J. M.; Johnson, M. R.; Le, V.-D.; Mangette, J. E.; Shenoy, R. A.; Stier, M. A. WO 2004/092134 A1, 2004;
62. Chem. Abstr. 141 2004 380131
63. Lin, L. S.; Doherty, G.; Shah, S. K.; Chang, L. L.; Hagmann, W. K.; Mumford, R. A. U.S. Patent 2003/0008861, 2003;
64. Chem. Abstr. 138 2003 90079
65. C.J. Blankley, J.S. Kaltenbronn, D.E. DeJhon, A. Werner, L.R. Bennett, G. Bobowski, U. Krolls, D.R. Johnson, W.M. Pearlman, M.L. Hoefle, A.D. Essenburg, D.M. Cohen, and H.R. Kaplan J. Med. Chem. 30 1987 992
66. F.J. Sayago, A.I. Jiménez, and C. Cativiela Tetrahedron: Asymmetry 18 2007 2358
67. CrysAlis RED Version 1.171.27 2005 Oxford Diffraction Ltd. Yarnton: England p8
68. G.M. Sheldrick SADABS: Empirical Absorption Correction Program 1996 Göttingen University Göttingen: Germany
69. G.M. Sheldrick SHELXS-86 Acta Crystallogr. A46 1990 467
70. G.M. Sheldrick SHELXL-97 Acta Crystallogr. A64 2008 112
71. H.E. Baumgarten, J.E. Dirks, J.M. Petersen, and R.L. Zey J. Org. Chem. 31 1966 3708