A facile and concise route toward the synthesis of novel imidazo-tetrazolodiazepinones via post-condensation modifications of the Ugi-azide adduct

作者：Medda Federico; Martinez Ariza Guillermo; Hulme Christopher^*

来源：Tetrahedron Letters, 2015, 56(38): 5295-5298.

DOI：10.1016/j.tetlet.2015.07.083

• Diazepinone
• Hydantoin
• Tetrazole
• Ugi reaction
• Multicomponent reaction
• UDC

This Letter describes novel methodology for the rapid assembly of unprecedented and likely biologically relevant imidazo-tetrazolodiazepinones. The product of a TMSN3-Ugi multi-component reaction is treated with an excess of isocyanate to generate 1,5-disubstituted tetrazolo-hydantoins functionalized with an internal-masked amino nucleophile previously introduced by the isocyanide input. Final products are obtained in good overall yields after microwave irradiation of the tetrazolo-hydantoin in acidic media. This methodology allows the production of complex polycyclic compounds in a mere three synthetic steps.

• 出版日期2015-9-16