A general approach to homochiral α-amino substituted bromo-heteroaromatics suitable for two-dimensional rapid analogue synthesis

Tetrahedron

Volumn 65, Issue 45, 2009, Pages 9487-9493

  Schultz Fademrecht, Carsten ^a   Kinzel, Olaf ^a   Markó, István E ^b   Pospisil, Tomas ^b   Pesci, Silvia ^a   Rowley, Michael ^a   Jones, Philip ^a  

^a IRBM   (Italy)

^b UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

2 [5 METHOXY 2 METHYL 1H INDOL 3 YL] N [1 [5 (NAPHTHALEN 2 YL)THIOPHEN 2 YL] 7 OXONONYL]ACETAMIDE; 2,4 DIBROMO 1 [[2 (TRIMETHYLSILYL)ETHOXY]METHYL] IMIDAZOLE; 2,5 DIBROMO 1 METHYL 1H PYRROLE; AROMATIC COMPOUND; HETEROCYCLIC COMPOUND; HISTONE DEACETYLASE INHIBITOR; IMIDAZOLE DERIVATIVE; N [1 [4 BROMO 1 [[2 (TRIMETHYLSILYL)ETHOXY]METHYL] 1H IMIDAZOL 2 YL] 6 [2 ETHYL 1,3 DIOXOLAN 2 YL]HEXYL] 2 METHYL PROPANE 2 SULFINAMIDE; N [1 [4 BROMO 1 [[2 (TRIMETHYLSILYL)ETHOXY]METHYL] 1H IMIDAZOL 2 YL] 6 [2 ETHYL 1,3 DIOXOLAN 2 YL]HEXYL] 2 METHYLPROPANE 2 SULFINAMIDE; N [1 [5 BROMO 1 METHYL 1H IMIDAZOL 2 YL] 6 (2 ETHYL 1,3 DIOXOLAN 2 YL)HEXYL] 2 METHYLPROPANE 2 SULFINAMIDE; N [1 [5 BROMO 1 METHYL 1H PYRROL 2 YL] 6 [2 ETHYL 1,3 DIOXOLAN 2 YL]HEXYL] 2 METHYLPROPANE 2 SULFINAMIDE; N [1 [5 BROMOFURAN 2 YL] 6 (2 ETHYL 1,3 DIOXOLAN 2 YL)HEXYL] 2 METHYLPROPANE 2 SULFINAMIDE; N [1 [5 BROMOTHIOPHEN 2 YL] 6 (2 ETHYL 1,3 DIOXOLAN 2 YL)HEXYL] 2 METHYLPROPANE 2 SULFINAMIDE; N [1 [5 BROMOTHIOPHEN 2 YL] 6 (2 ETHYL 1,3 DIOXOLAN 2 YL)HEXYL] 2-METHYLPROPANE 2 SULFINAMIDE; N [1 [5 BROMOTHIOPHEN 2 YL] 7 OXONONYL] 2 METHYLPROPANE METHYLPROPANE 2 SULFINAMIDE; N [1 [6 BROMOPYRIDIN 2 YL] 6 (2 ETHYL 1,3 DIOXOLAN 2 YL)HEXYL] 2 METHYLPROPANE 2 SULFINAMIDE; N [6 (2 ETHYL 1,3 DIOXOLAN 2 YL)HEXYLIDENE] 2 METHYL METHYLPROPANE 2 SULFINAMIDE; N [6 [2 ETHYL 1,3 DIOXOLAN 2 YL] 1 [4 [2 NAPHTHYL] 1 [[2 (TRIMETHYLSILYL) ETHOXY]METHYL] 1H IMIDAZOL 2 YL]HEXYL] 2 METHYLPROPANE 2 SULFINAMIDE; N [6 [2 ETHYL 1,3 DIOXOLAN 2 YL] 1 [5 (NAPHTHALEN 2 YL)FURAN 2 YL]HEXYL] 2 METHYLPROPANE 2 SULFINAMIDE; N [6 [2 ETHYL 1,3 DIOXOLAN 2 YL] 1 [5 (NAPHTHALEN 2 YL]THIOPHEN 2 YL)HEXYL] 2 METHYLPROPANE 2 SULFINAMIDE; N [6 [2 ETHYL 1,3 DIOXOLAN 2 YL] 1 [6 (NAPHTHALEN 2 YL)PYRIDIN 2 YL]HEXYL] 2 METHYLPROPANE 2 SULFINAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHIRALITY; DEPROTECTION REACTION; DERIVATIZATION; PRIORITY JOURNAL; STEREOCHEMISTRY; SUBSTITUTION REACTION; SUZUKI REACTION; SYNTHESIS;

EID: 70349974386     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.08.013     Document Type: Article

References (19)

1. Jones P., Altamura S., De Francesco R., Gonzelez Paz O., Kinzel O., Mesiti G., Monteagudo E., Pescatore G., Rowley M., Verdirame M., and Steinkuhler C. J. Med. Chem. 51 (2008) 2350
2. Ellman J.A., Owens T.D., and Tang T.P. Acc. Chem. Res. 35 (2002) 984
3. Borg G., Chino M., and Ellman J.A. Tetrahedron Lett. 42 (2001) 1433
4. Cogan D.A., Liu G., and Ellman J.A. Tetrahedron 55 (1999) 8883
5. Cogan D.A., Liu G., and Ellman J.A. J. Am. Chem. Soc. 121 (1999) 268
6. Liu G., Cogan D.A., and Ellman J.A. J. Am. Chem. Soc. 119 (1997) 9913
7. Cheng L., Liu L., Sui Y., Wang D., and Chen Y.-J. Tetrahedron: Asymmetry 18 (2007) 1833
8. Hashmi A.S.K., Schäfer S., Bats J.W., Frey W., and Rominger F. Eur. J. Org. Chem. (2008) 4891
9. Andreassen T., Hansen L.-K., and Gautun O.R. Eur. J. Org. Chem. (2008) 4871
10. 4 was obtained by ketone protection and subsequent amide formation by standard methods starting from commercial 7-oxo-nonanoic acid.
11. Liu G., Cogan D.A., Owens T.D., Tang T.P., and Ellman J.A. J. Org. Chem. 64 (1999) 1278
12. The chiral (R)-N-tert-butanesulfinyl-imine 1 was relatively stable and could be purified by flash chromatograhy on silica gel.
13. Davis F.A., and McCoull W. J. Org. Chem. 64 (1999) 3396
14. An excess of 2,5-dibromothiophene (1.4 equiv) was stirred with n-BuLi (1.1 equiv) at -78 °C for 1 h. After addition of 1 (1.0 equiv) at -78 °C the reaction mixture was stirred for 16 h, raising the temperature to room temperature.
15. Seco J.M., Quiñoá E., and Riguera R. Chem. Rev. 104 (2004) 17
16. Ohtani I., Kusumi T., Kashman Y., and Kakisawa H. J. Am. Chem. Soc. 113 (1991) 4092
17. Dale J., and Mosher H. J. Am. Chem. Soc. 95 (1973) 512
18. Barder T.E., Walker S.D., Martinelli J.R., and Buchwald S.L. J. Org. Chem. 127 (2005) 4685
19. Walker D.W., Barder T.E., Martinelli J.R., and Buchwald S.L. Angew. Chem., Int. Ed. 43 (2004) 1871