A regioselective one-pot method for the synthesis of 1-ethyl 2,4-dihydrochromene[3,4-c]pyrroles in 63–94% yields from available 2-phenyl-, 2-trifluoro(trichloro)methyl- or 2-phenyl-2-(trifluoromethyl)-3-nitro-2H-chromenes and ethyl isocyanoacetate through the Barton–Zard reaction in ethanol at reflux for 0.5 h, using K2CO3 as a base, has been developed.
Endo-1,3-Dipolar cycloaddition of azomethine ylides generated in situ from 11H-indeno[1,2-b]quinoxalin-11-one and L-proline/thiaproline to (E)-1,5-diarylpent-4-ene-1,3-diones led to the 3-hydroxy-3-aryl-1-(1′-arylspiro[indeno[1,2-b]quinoxaline-11,3′-(thia)pyrrolizidin]-2′-yl)prop-2-en-1-ones containing the 1,3-diketone fragment. Upon processing of these adducts with arylhydrazine hydrochlorides in an acidic medium, the 2′-(1,3-diaryl-1H-pyrazol-5-yl)-1′-arylspiro[indeno[1,2-b]quinoxaline-11,3′-pyrrolizidines] were formed as individual regioisomers. In a similar reaction with hydrazine hydrate and hydroxylamine, the corresponding hybrids bearing the N-unsubstituted pyrazole and isoxazole moieties were obtained. Most of spiro[indenoquinoxaline-pyrrolizidine]-N-arylpyrazole conjugates have shown high cytotoxic activity against the HeLa cancer cell line.
1 April 2017 in Chemistry of Heterocyclic Compounds