Iodocyclization of o -alkynylbenzamides revisited: Formation of isobenzofuran-1(3 H)-imines and 1 H -isochromen-1-imines instead of lactams

Journal of Organic Chemistry

Volumn 77, Issue 22, 2012, Pages 10118-10124

  Schlemmer, Claudine ^a   Andernach, Lars ^a   Schollmeyer, Dieter ^a   Straub, Bernd F ^b   Opatz, Till ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

^b UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BULKY SUBSTITUENTS; ELECTROPHILES; IODOCYCLIZATION; NUCLEOPHILIC ATTACK; STERIC HINDRANCES; TRIPLE BONDS;

NITROGEN COMPOUNDS;

AMIDES;

ALKYNYL GROUP; AMIDE; BENZAMIDE DERIVATIVE; ELECTROPHILE; ISOBENZOFURAN DERIVATIVE; LACTAM; NITROGEN; OXYGEN;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CYCLIZATION;

EID: 84869193060     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo3017378     Document Type: Article

References (40)

1. Yao, T.; Larock, R. C. J. Org. Chem. 2003, 68, 5936
2. Cherry, K.; Thibonnet, J.; Duchêne, A.; Parrain, J.-L.; Abarbri, M. Tetrahedron Lett. 2004, 45, 2063
3. Yao, T.; Larock, R. C. J. Org. Chem. 2005, 70, 1432
4. Robin, S.; Rousseau, G. Tetrahedron 1998, 54, 13681
5. Hashmi, A. S. K.; Hutchings Graham, J. Angew. Chem., Int. Ed. 2006, 45, 7896
6. Gimeno, A.; Medio-Simón, M.; de Arellano, C. R. r.; Asensio, G.; Cuenca, A. B. Org. Lett. 2010, 12, 1900
7. Mehta, S.; Waldo, J. P.; Larock, R. C. J. Org. Chem. 2009, 74, 1141
8. Chen, D.; Song, G.; Jia, A.; Li, X. J. Org. Chem. 2011, 76, 8488
9. Jithunsa, M.; Ueda, M.; Miyata, O. Org. Lett. 2011, 13, 518
10. Xie, Y.-X.; Yan, Z.-Y.; Wang, D.-Z.; Wu, L.-Y.; Qian, B.; Liu, X.-Y.; Liang, Y.-M. Eur. J. Org. Chem. 2009, 2283
11. Bubar, A.; Estey, P.; Lawson, M.; Eisler, S. J. Org. Chem. 2012, 77, 1572
12. Zhao, P.; Chen, D.; Song, G.; Han, K.; Li, X. J. Org. Chem. 2011, 77, 1579
13. Khan, M. W.; Kundu, N. G. Synlett 1997, 12, 1435
14. Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652
15. Hiroya, K.; Itoh, S.; Sakamoto, T. J. Org. Chem. 2004, 69, 1126
16. Sakai, N.; Annaka, K.; Fujita, A.; Sato, A.; Konakahara, T. J. Org. Chem. 2008, 73, 4160
17. Hashmi, A. S. K.; Schuster, A. M.; Rominger, F. Angew. Chem. 2009, 121, 8396
18. Bian, M.; Yao, W.; Ding, H.; Ma, C. J. Org. Chem. 2010, 75, 269
19. Parvatkar, P. T.; Parameswaran, P. S.; Tilve, S. G. Chem.-Eur. J. 2012, 18, 5460
20. K. Banerjee, A.; S. Laya, M.; V. Cabrera, E. Curr. Org. Chem. 2011, 15, 1058
21. Wiebe, C.; Schlemmer, C.; Weck, S.; Opatz, T. Chem. Commun. 2011, 47, 9212
22. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467
23. Wang, C.; Lu, J.; Mao, G.; Xi, Z. J. Org. Chem. 2005, 70, 5150
24. Ma, S.; Xie, H. Tetrahedron 2005, 61, 251
25. Ma, S.; Xie, H. J. Org. Chem. 2002, 67, 6575
26. Lemieux, R. U.; Morgan, A. R. Can. J. Chem. 1965, 43, 2190
27. Homsi, F.; Rousseau, G. J. Org. Chem. 1998, 63, 5255
28. Grimme, S.; Ehrlich, S.; Goerigk, L. J. Comput. Chem. 2011, 32, 1456
29. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650
30. Frisch, M. J.; Pople, J. A.; Binkley, J. S. J. Chem. Phys. 1984, 80, 3265
31. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299
32. Jaguar, version 7.9; Schrödinger, LLC: New York, 2011.
33. Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1996, 77, 3865
34. Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1997, 78, 1396
35. Frisch, M. J.; Pople, J. A.; Binkley, J. S. J. Chem. Phys. 1984, 80, 3265
36. Seeman, J. I. Chem. Rev. 1983, 83, 83
37. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734
38. Duffault, J.-M.; Tellier, F. Synth. Commun. 1998, 28, 2467
39. Kundu, N. G.; Khan, M. W. Tetrahedron 2000, 56, 4777
40. Sakamoto, T.; An-Naka, M.; Kondo, Y.; Yamanaka, H. Chem. Pharm. Bull. 1986, 34, 2754