Hydriodic acid-mediated cyclization of a-substituted secondary 2-ethenylbenzamides: Synthesis of 2-substituted 2,3-dihydro-3,3-dimethyl-1H- isoindol-1-ones and 3,3-disubstituted (E)-1-(arylimino)-1,3- dihydroisobenzofurans

Helvetica Chimica Acta

Volumn 93, Issue 7, 2010, Pages 1274-1280

  Kobayashi, Kazuhiro ^a   Fujita, Seiki ^a   Nakai, Daisuke ^a   Fukumoto, Shogo ^a   Fukamachi, Shuhei ^a   Konishi, Hisatoshi ^a  

^a TOTTORI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZAMIDES; FACILE METHOD; HYDRIODIC ACID; ROOM TEMPERATURE;

AMIDES; CYCLIZATION; HYDROCARBONS;

ACIDS;

1 [(4 BROMOPHENYL)IMINO] 1,3 DIHYDRO 3 METHYL 3 PHENYLISOBENZOFURAN; 1 [(4 CHLOROPHENYL)IMINO] 1,3 DIHYDRO 3 METHYL 3 (4 METHYLPHENYL)ISOBENZOFURAN; 1 [(4 CHLOROPHENYL)IMINO] 1,3 DIHYDRO 3 METHYL 3 PHENYLISOBENZOFURAN; 1,3 DIHYDRO 5 METHOXY 3 METHYL 3 PHENYL 1 (PHENYLIMINO)ISOBENZOFURAN; 2 (1,1 DIMETHYLETHYL) 2,3 DIHYDRO 5 METHOXY 3,3 DIMETHYL 1H ISOINDOL 1 ONE; 2 (4 CHLOROPHENYL) 2,3 DIHYDRO 3,3 DIMETHYL 1H ISOINDOL 1 ONE; 2,3 DIHYDRO 3 METHYL 3 PHENYL 1 (PHENYLIMINO)ISOBENZOFURAN; 2,3 DIHYDRO 3,3 DIMETHYL 2 PHENYL 1H ISOINDOL 1 ONE; 2,3 DIHYDRO 5,6 DIMETHOXY 3,3 DIMETHYL 2 PHENYL 1H ISOINDOL 1 ONE; 3 ETHYL 1,3 DIHYDRO 3 PHENYL 1 (PHENYLIMINO)ISOBENZOFURAN; ACID; BENZAMIDE DERIVATIVE; HYDRIODIC ACID; ISOBENZOFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; ROOM TEMPERATURE; SUBSTITUTION REACTION;

EID: 77954911254     PISSN: 0018019X     EISSN: 15222675     Source Type: Journal    
DOI: 10.1002/hlca.201000172     Document Type: Article

References (22)

1. K. Kobayashi, M. Hase, K. Hashimoto, S. Fujita, M. Tanmatsu, O. Morikawa, H. Konishi, Synthesis 2006, 2493.
2. N. Kanamitsu, T. Osaki, Y. Itsuji, M. Yoshimura, H. Tsujimoto, M. Soga, Chem. Pharm. Bull. 2007, 55, 1682;
3. T. Nishiyama, S. Chiba, Y. Yamada, Eur. J. Pharmacol. 2008, 596, 56; see also pertinent refs. cited in [1].
4. T. Tsuritani, S. Kii, A. Akao, K. Sato, N. Nonoyama, T. Mase, N. Yasuda, Synlett 2006, 801;
5. A. Couture, E. Deniau, M. Lamblin, M. Lorion, P. Grandclaudon, Synthesis 2007, 1434;
6. M. Lamblin, A. Couture, E. Deniau, P. Grandclaudon, Tetrahedron 2007, 63, 2664;
7. M. Lamblin, A. Couture, E. Deniau, P. Grandclaudon, Tetrahedron: Asymmetry 2008, 19, 111;
8. C. S. Cho, W. X. Ren, Tetrahedron Lett. 2009, 50, 2097; see also pertinent refs. cited in [1].
9. a) H. Yoshida, H. Fukushima, J. Ohshima, A. Kunai, Angew. Chem., Int. Ed. 2004, 43, 3935;
10. b) C. G. Saluste, S. Crumpler, M. Furber, R. J. Whitby, Tetrahedron Lett. 2004, 45, 6995;
11. c) H. Yoshida, H. Fukushima, T. Morishita, J. Ohshita, A. Kunai, Tetrahedron 2007, 63, 4793.
12. H. Zhang, S. Zhang, L. Liu, G. Luo, W. Duan, W. Wang, J. Org. Chem. 2010, 75, 368; see also pertinent refs. cited in this article and [13c].
13. I. Fleming, M. Woolias, J. Chem. Soc., Perkin Trans. 1 1979, 829.
14. G.W. Morrow, T. M. Marks, D. L. Sear, Tetrahedron 1995, 51, 10115.
15. M. E. Jason, Tetrahedron Lett. 1982, 23, 1635.
16. S. Fukamachi, H. Konishi, K. Kobayashi, Heterocycles 2009, 78, 169.
17. K. Kobayashi, S. Fujita, M. Hase, O. Morikawa, H. Konishi, Bull. Chem. Soc. Jpn. 2007, 80, 763.
18. K. Kobayashi, S. Fujita, H. Konishi, Heterocycles 2008, 75, 2555.
19. W. E. Parham, C. K. Bradsher, D. C. Reames, J. Org. Chem. 1981, 46, 4804.
20. a) F. N. Jones, C. R. Hauser, J. Org. Chem. 1962, 27, 3364;
21. b) Y. Kondo, M. Asai, T. Miura, M. Uchiyama, T. Sakamoto, Org. Lett. 2001, 3, 13;
22. c) K. Kobayashi, T. Kozuki, S. Fukamachi, H. Konishi, Heterocycles 2010, 81, 163.