A scalable and efficient approach to the synthesis of fused and spirocyclic sp 3-enriched isoxazoline building blocks via the 1,3-dipolar cycloaddition of functionalized chloroximes and cyclic alkenes is disclosed. The target co...
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Basicity‐Controlled [3+2] Cyclization of 3‐Hydroxyquinolin‐ones and β‐Chlorinated Nitrostyrenes
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The construction of intriguing scaffolds through the recombination of natural products fragments are important both in organic and medicinal chemistry. Herein, a basicity-controlled synthesis of (dihydro)furo[2,3-c]quinolin-4(5H)-one derivatives through (3+2) cyclization between 3-hydroxyquinolin-2-ones and β-chlorinated nitrostyrenes was developed.
Abstract
The construction of novel skeletons through the recombination of natural products ring systems is attractive. Herein, a basicity-controlled synthesis of (dihydro)furo[2,3-c]quinolin-4(5H)-one derivatives through (3+2) cyclization between 3-hydroxyquinolin-2-ones and β-chlorinated nitrostyrenes was developed. In addition, preliminary study gave the chiral dihydrofuro[2,3-c]quinolin-4(5H)-one derivatives with up to 83 % ee.
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