PdI2/I2-catalyzed thiolation-annulation of 2-alkynylbenzyl azides with disulfides: Selective synthesis of 4-sulfenylisoquinolines

Synthesis

Volumn , Issue 8, 2011, Pages 1219-1226

  Zhang, Hong Ping ^a,b   Yang, Xu Heng ^a   Peng, Peng ^a   Li, Jin Heng ^a  

^a HUNAN NORMAL UNIVERSITY   (China)

^b SHAOYANG UNIVERSITY   (China)

Author keywords

2 alkynylbenzyl azides; Annulation; Disulfides; Iodine; Isoquinolines; Palladium; Thiolation

Indexed keywords

2-ALKYNYLBENZYL AZIDES; ANNULATION; DISULFIDES; ISOQUINOLINES; THIOLATION;

ACETYLENE; CATALYSIS; INDUSTRIAL CHEMICALS; IODINE;

NITROGEN COMPOUNDS;

2 ALKYNYLBENZYLAZIDE; 4 SULFENYLISOQUINOLINE; AZIDE; DISULFIDE; IODINE; ISOQUINOLINE DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; SYNTHESIS; THIOLATION;

EID: 79953789284     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1259965     Document Type: Article

References (49)

1. For selected reviews, see:, Larock R C., Pure Appl. Chem. 1999 71 1435
2. Zeni G, Larock R C., Chem. Rev. 2006 106 4644
3. Larock R C., Top. Organomet. Chem. 2005 14 147
4. lvarez-Corral M, Muoz-Dorado M, Rodrguez-Garca I, Chem. Rev. 2008 108 3174
5. Patil N T., Yamamoto Y, Chem. Rev. 2008 108 3395
6. Yamamoto Y, Gridnev I D., Patil N T., Jin T, Chem. Commun. 2009 5075
7. Guo L.-N, Duan X.-H, Liang Y.-M, Acc. Chem. Res. 2011 44 111
8. Dai G, J. Org. Chem. 2003 68 920
9. Dai G, Larock R C., J. Org. Chem. 2002 67 7042
10. Roesch K R., Larock R C., J. Org. Chem. 2002 67 86
11. Roesch K R., Zhang H, Larock R C., J. Org. Chem. 2001 66 8042
12. Sudipta R, Sujata R, Benjamin N, David H, Larock R C., J. Comb. Chem. 2009 11 1061
13. Huang Q, Larock R C., J. Org. Chem. 2003 68 980
14. Roesch K R., Larock R C., Org. Lett. 1999 1 553
15. Roesch K R., Zhang H, Larock R C., J. Org. Chem. 1998 63 5306
16. Huang Q, Larock R C., J. Org. Chem. 2002 67 3437
17. Huang Q, Hunter J A., Larock R C., Org. Lett. 2001 3 2973
18. Korivi R P., Cheng C.-H, Org. Lett. 2005 7 5179
19. Bajracharya G B., Pahadi N K., Gridnev I D., Yamamoto Y, J. Org. Chem. 2006 71 6204
20. Niu Y.-N, Yan Z.-Y, Gao G.-L, Wang H.-L, Shu X.-Z, Ji K.-G, Liang Y.-M, J. Org. Chem. 2009 74 2893
21. Lim S.-G, Lee J H., Moon C W., Hong J.-B, Jun C.-H, Org. Lett. 2003 5 2759
22. Guimond N, Fagnou K, J. Am. Chem. Soc. 2009 131 12050
23. Wang B, Lu B, Jiang Y, Zhang Y, Ma D, Org. Lett. 2008 10 2761
24. Huo Z, Yamamoto Y, Tetrahedron Lett. 2009 50 3651
25. Ramakrishna T V. V., Sharp P R., Org. Lett. 2003 5 877
26. Fischer D, Tomeba H, Pahadi N K., Patil N T., Yamamoto Y, Angew. Chem. Int. Ed. 2007 46 4764
27. Fischer D, Tomeba H, Pahadi N K., Patil N T., Huo Z, Yamamoto Y, J. Am. Chem. Soc. 2008 130 15720
28. Huo Z, Gridnev I D., Yamamoto Y, J. Org. Chem. 2010 75 1266
29. Zhang H.-P, Yu S.-C, Liang Y, Peng P, Tang B.-X, Li J.-H, Synlett 2011 DOI: 10.1055/s-0030-1259722
30. For selected examples of constructing the isoquinoline skeleton by other transformations, see:, Cox E D., Cook J M., Chem. Rev. 1995 95 1797
31. Chrzanowska M, Rozwadowska M D., Chem. Rev. 2004 104 3341
32. Youn S W., J. Org. Chem. 2006 71 2521
33. Boudou M, Enders D, J. Org. Chem. 2005 70 9486
34. Pandy G, Balakrishnan M, J. Org. Chem. 2008 73 8128
35. The Chemistry of Hetrocyclic Compounds: Isoquinolines Vol. 38 Coppola G M. Schuster H F. Wiley New York 1981 Part 3
36. The Chemistry and Biology of Isoquinoline Alkaloids Phillipson J D. Roberts M F. Zenk M H. Springer Verlag Berlin 1985
37. Bentley K W., The Isoquinoline Alkaloids Vol. 1 Hardwood Academic Amsterdam 1998
38. Kletsas D, Li W, Han Z, Papadopoulos V, Biochem. Pharmacol. 2004 67 1927
39. Mach U R., Hackling A E., Perachon S, Ferry S, Wermuth C G., Schwartz J.-C, Sokoloff P, Stark H, ChemBioChem 2004 5 508
40. Muscarella D E., O'Brain K A., Lemley A T., Bloom S E., Toxicol. Sci. 2003 74 66
41. Dzierszinski F, Coppin A, Mortuaire M, Dewally E, Slomianny C, Ameisen J.-C, DeBels F, Tomavo S, Antimicrob. Agents Chemother. 2002 46 3197
42. Kartsev V G., Med. Chem. Res. 2004 13 325
43. Baker B J., Alkaloids: Chem. Biol. Perspectives 1996 10 357
44. For papers on the use of disulfides from our group, see:, Wang Z.-L, Tang R.-Y, Luo P.-S, Deng C.-L, Zhong P, Li J.-H, Tetrahedron 2008 64 10670
45. Luo P.-S, Yu M, Tang R.-Y, Zhong P, Li J.-H, Tetrahedron Lett. 2009 50 1066
46. Luo P.-S, Wang F, Li J.-H, Tang R.-Y, Zhong P, Synthesis 2009 921
47. Du H.-A, Zhang X.-G, Tang R.-Y, Li J.-H, J. Org. Chem. 2009 74 7844
48. Guo Y.-J, Tang R.-Y, Li J.-H, Zhong P, Zhang X.-G, Adv. Catal. Synth. 2009 351 2615
49. Fang X.-L, Tang R.-Y, Zhong P, Li J.-H, Synthesis 2009 4183