Synthesis of extended, π-conjugated isoindolin-1-ones

Journal of Organic Chemistry

Volumn 77, Issue 3, 2012, Pages 1572-1578

  Bubar, Alex ^a   Estey, Paula ^a   Lawson, Michael ^a   Eisler, Sara ^a  

^a UNIVERSITY OF NEW BRUNSWICK   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CONJUGATED MOLECULES; CYCLIZATIONS; CYCLIZED PRODUCTS; HIGH YIELD; ISOINDOLINONE; STEREOSPECIFICITY; STRUCTURAL ALTERATIONS;

ACETYLENE; AMIDES;

SYNTHESIS (CHEMICAL);

ISOINDOLE DERIVATIVE; ISOINDOLIN 1 ONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL PARAMETERS; CHEMICAL STRUCTURE; CONJUGATION; CYCLIZATION; DEPROTECTION REACTION; NUCLEOPHILICITY; REGIOSPECIFICITY; SONOGASHIRA REACTION; STEREOSPECIFICITY; SYNTHESIS;

CHEMISTRY TECHNIQUES, SYNTHETIC; CYCLIZATION; ISOINDOLES;

EID: 84856647895     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2021345     Document Type: Article

References (33)

1. Hardcastle, I. R.; Liu, J.; Valeur, E.; Watson, A.; Ahmed, S. U.; Blackburn, T. J.; Bennaceur, K.; Clegg, W.; Drummond, C.; Endicott, J. A.; Golding, B. T.; Griffin, R. J.; Gruber, J.; Haggerty, K.; Harrington, R. W.; Hutton, C.; Kemp, S.; Lu, X.; McDonnell, J. M.; Newell, D. R.; Noble, M. E. M.; Payne, S. L.; Revill, C. H.; Riedinger, C.; Xu, Q.; Lunec, J. J. Med. Chem. 2011, 54, 1233-1243
2. Comins, D. L.; Schilling, S.; Zhang, Y. Org. Lett. 2005, 7, 95-98
3. Kundu, N. G.; Khan, M. W. Tetrahedron 2000, 56, 4777-4792
4. Belluau, V.; Noeureuil, P.; Ratzke, E.; Skvortsov, A.; Gallagher, S.; Motti, C. A.; Oelgemöller, M. Tetrahedron Lett. 2010, 51, 4738-4741
5. Mori, M.; Chiba, K.; Ban, Y. J. Org. Chem. 1978, 43, 1684-1687
6. Yao, T.; Larock, R. C. J. Org. Chem. 2005, 70, 1432-1437
7. Deniau, E.; Couture, A.; Grandclaudon, P. Tetrahedron: Asymmetry 2008, 19, 2735-2740
8. Kobayashi, K.; Matsumoto, K.; Nakamura, D.; Fukamachi, S.; Konishi, H. Helv. Chim. Acta 2010, 93, 1048-1051
9. Sun, C.; Xu, B. J. Org. Chem. 2008, 73, 7361-7364
10. Wu, M.-J.; Chang, L.-J.; Wei, L.-M.; Lin, C.-F. Tetrahedron 1999, 55, 13193-13200
11. Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285-2310
12. Bronstein, H.; Chen, Z.; Ashraf, R. S.; Zhang, W.; Du, J.; Durrant, J. R.; Tuladhar, P. S.; Song, K.; Watkins, S. E.; Geerts, Y.; Wienk, M. M.; Janssen, R. A. J.; Anthopoulos, T.; Sirringhaus, H.; Heeney, M.; McCulloch, I. J. Am. Chem. Soc. 2011, 133, 3272-3275
13. Loser, S.; Bruns, C. J.; Miyauchi, H.; Ortiz, R. P.; Facchetti, A.; Stupp, S.; Marks, T. J. J. Am. Chem. Soc. 2011, 133, 8142-8145
14. Lei, T.; Cao, Y.; Fan, Y.; Liu, C.-J.; Yuan, S.-C.; Pei, J. J. Am. Chem. Soc. 2011, 133, 6099-6101
15. Mehta, S.; Waldo, J. P.; Larock, R. C. J. Org. Chem. 2009, 74, 1141-1147
16. Kundu, N. G.; Khan, M. W.; Mukhopadhyay, R. Tetrahedron 1999, 55, 12361-12376
17. Vasilevsky, S. F.; Mikhailovskaya, T. F.; Mamatyuk, V. I.; Salnikov, G. E.; Bogdanchikov, G. A.; Manoharan, M.; Alabugin, I. V. J. Org. Chem. 2009, 74, 8106-8117
18. Chen, D.; Song, G.; Jia, A.; Li, X. J. Org. Chem. 2011, 76, 8488-8494
19. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467-4470
20. Koseki, Y.; Kusano, S.; Sakata, H.; Nagasaka, T. Tetrahedron Lett. 1999, 40, 2169-2172
21. Jacobi, P. A.; Brielmann, H. L.; Hauck, S. I. J. Org. Chem. 1996, 61, 5013-5023
22. Alabugin, I. V.; Gilmore, K.; Manoharan, M. J. Am. Chem. Soc. 2011, 133, 12608-12623
23. Yasuhara, A.; Kanamori, Y.; Kaneko, M.; Numata, A.; Kondo, Y.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 529-534
24. Clark, J. H. Chem. Rev. 1980, 80, 429-452
25. Onitsuka, K.; Fujimoto, M.; Kitajima, H.; Ohshiro, N.; Takei, F.; Takahashi, S. Chem.-Eur. J. 2004, 10, 6433-6446
26. Chen, G.; Mahmud, I.; Dawe, L. N.; Daniels, L. M.; Zhao, Y. J. Org. Chem. 2011, 76, 2701-2715
27. Hay, A. S. J. Org. Chem. 1962, 27, 3320-3321
28. Lamblin, M.; Couture, A.; Deniau, E.; Grandclaudon, P. Org. Biomol. Chem. 2007, 5, 1466-1471
29. Chan, S.-H.; Chao, T.-C.; Ko, B.-T.; Chen, C.-P.; Lin, C.-S.; Chen, Y.-L.; Yu, C.-Y. (Industrial Technology Research Institute, Taiwan). Soluble polythiophene derivatives containing highly coplanar repeating units for use in optoelectronic devices. US Patent 7,754,847, July 1, 2010.
30. Rasolofonjatovo, E.; Provot, O.; Hamze, A.; Bignon, J.; Thoret, S.; Brion, J.-D.; Alami, M. Eur. J. Med. Chem. 2010, 45, 3617-3626
31. Orita, A.; An, D. L.; Nakano, T.; Yaruva, J.; Ma, N.; Otera, J. Chem.-Eur. J. 2002, 8, 2005-2010
32. Cherry, K.; Duchene, A.; Thibonnet, J.; Parrain, J.-L.; Abarbri, M. Synthesis 2005, 14, 2349-2356
33. Zhao, Y.-L.; Liu, L.; Zhang, W.; Sue, C.-H.; Li, Q.; Miljanic, O. S.; Yaghi, O. M.; Stoddart, J. F. Chem.-Eur. J. 2009, 15, 13356-13380