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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
One-Pot Regioselective Synthesis of Spiroimidazolidinones via a Sequential Ugi 4CR/Azide-Isocyanide
Yan-Mei Yan1, Hong-Bo Tong2, Zhen-Xing Ren2
1College of Chemistry and Materials, Taiyuan Normal University, Jinzhong 030619, P. R. of China.
Abstract:
Herein a novel and robust methodology to spiroimidazolidinones has been developed under a mild reaction. The reaction of (Z)-2-azido-3-phenylacrylic acids 1, aldehydes 2, amines 3, isocyanides 4, and isocyanides 6 produced regioselectively spiroimidazolidinones in 71-88% yields via a sequential Ugi 4CR/Pd(0) catalyzed azide-isocyanide coupling/cyclization/rearrangement/hydroxylation reaction. Furthermore, the easily accessible starting materials, high bond-forming efficiency, and broad substituent tolerance make this strategy useful in synthetic and medicinal chemistry.
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