Reacción #1098642

ord-d0e9774e6dab472ca9f66e0df4b78246

Ecuación de reacción

C#CCn1ccnc1[N+](=O)[O-]
2-Nitro-1-(prop-2-ynyl)-1H-imidazole
CC(=O)OC(CN=[N+]=[N-])COS(=O)(=O)c1ccc(C)cc1
1-azido-3-(tosyloxy)propan-2-yl acetate
CC(=O)OC(CN=[N+]=[N-])COS(=O)(=O)c1ccc(C)cc1
1-Azido-3-(tosyloxy)propan-2-yl acetate
→
CC(=O)OC(COS(=O)(=O)c1ccc(C)cc1)Cn1cc(Cn2ccnc2[N+](=O)[O-])nn1
16
CC(=O)OC(COS(=O)(=O)c1ccc(C)cc1)Cn1cc(Cn2ccnc2[N+](=O)[O-])nn1
1-(4-((2-Nitro-1H-imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)-3-(tosyloxy)propan-2-yl acetate

Reactantes

C#CCn1ccnc1[N+](=O)[O-]
2-Nitro-1-(prop-2-ynyl)-1H-imidazole
CC(=O)OC(CN=[N+]=[N-])COS(=O)(=O)c1ccc(C)cc1
1-azido-3-(tosyloxy)propan-2-yl acetate
CC(=O)OC(CN=[N+]=[N-])COS(=O)(=O)c1ccc(C)cc1
1-Azido-3-(tosyloxy)propan-2-yl acetate

Reactivos

Ninguno

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe residue is purified by chromatography on silica gel (MeOH/CH2Cl2, 1:10)

Procedimiento

2-Nitro-1-(prop-2-ynyl)-1H-imidazole 10 (0.2 g, 1.32 mmol) is heated with 1-azido-3-(tosyloxy)propan-2-yl acetate 15 (0.41 g, 1.32 mmol) at 60° C. overnight. The residue is purified by chromatography on silica gel (MeOH/CH2Cl2, 1:10) to afford 16.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07977361B2uspto-grants-2011_07