A novel allylic substitution strategy to four-component synthesis of pyrazole-substituted fused pyrroles

作者：Tu Xing Chao; Fan Wei; Jiang Bo^*; Wang Shu Liang; Tu Shu Jiang

来源：Tetrahedron, 2013, 69(30): 6100-6107.

DOI：10.1016/j.tet.2013.05.063

• Multicomponent domino reactions
• Pyrazole-substituted fused pyrroles
• Microwave heating
• Allylic pyrazolization

The selective formation of pyrazole-substituted fused pyrroles through HOAc-mediated multicomponent reactions of enaminones with arylglyoxal monohydrates and generated in situ pyrazole-3-carboxylates was developed. It constructed a variety of bis-heterocyclic pairs under mild conditions in a domino process. Reaction driving tandem cyclization/allylic esterification/allylic substitution was achieved through the formation of in situ generation of allyl esters and pyrazole-3-carboxylates from readily available starting materials. Up to two new five-membered heterocyclic rings and five new sigma bonds including a C(sp3)-C(sp2) bond were formed in a single reaction without isolated intermediates.

• 出版日期2013-7-29