Molecular Hybridization-Guided One-Pot Multicomponent Synthesis of Turmerone Motif-Fused 3,3′-Pyrrolidinyl-dispirooxindoles via a 1,3-Dipolar Cycloaddition Reaction

Bing Lin, Gen Zhou, Yi Gong, Qi-Di Wei, Min-Yi Tian, Xiong-Li Liu, Ting-Ting Feng, Ying Zhou, Wei-Cheng Yuan
2017 Molecules  
Described herein is the development of a facile and efficient methodology for the synthesis of novel turmerone motif-fused 3,3 -pyrrolidinyl-dispirooxindoles 3-5 via a multicomponent 1,3-dipolar cycloaddition of dienones 2 with azomethine ylides (thermally generated in situfrom isatins and proline or thioproline or sarcosine). Products bearing four or three consecutive stereocenters consist of two oxindole moieties and a pyrrolidinyl core, including vicinal spiroquaternary stereocenters fused
more » ... ereocenters fused in one ring structure were smoothly obtained in high yields (up to 93% yield) with good diastereoselectivity (up to >20:1). Another valuable application of this method was for the design of new hybrid architectures for biological screening through the adequate fusion of these sub-units of turmerone and 3,3 -pyrrolidinyl-dispirooxindole, generating drug-like molecules. Molecules 2017, 22, 645 2 of 27 arylidenemalonodinitriles [60], α,β-unsaturated lactones [61] nitrostyrenes [62], acrylamides [63] and various other electron-deficient alkenes [45, 64, 65] have been documented. In view of their unique structural features and inspiring biological activities, the development of novel methods for the synthesis of 3,3 -pyrrolidinyl-dispirooxindoles is desirable (Figure 1 ). Molecules 2017, 22, 645 2 of 27 biological activities, the development of novel methods for the synthesis of 3,3′-pyrrolidinyldispirooxindoles is desirable (Figure 1 ).
doi:10.3390/molecules22040645 pmid:28420177 fatcat:zvwwts2nxfcu7dwdbhsafzp2rm