A convergent route to structures with multiple contiguous carbon-nitrogen bonds. The divergent role of N-acyl groups

作者：Han Songzhe; Zard Samir Z^*

来源：Tetrahedron, 2016, 72(48): 7859-7865.

DOI：10.1016/j.tet.2016.05.085

• Radical addition
• Xanthates
• Tetra-amines
• Imidazolinones

The radical addition of xanthates to N,N-diacetyl imidazol-2-one can be followed by a second addition to N,N-di-Boc imidazol-2-one to give after reductive dexanthylation a protected tetra -amine possessing four contiguous carbon nitrogen bonds, or even five if the starting xanthate itself bears a protected amine. The success of this sequence hinges on the difference in radical stability between radicals substituted by an N-acyl and N-carbamoyl nitrogens, which allows control of the radical addition and prevents the formation of oligomers.

• 出版日期2016-12-1