Regio- and Stereoselective 1,3-dipolar Cycloaddition of Azomethine Ylides Based on Isatins and (thia)proline to 3-nitro-2-(trifluoro(trichloro)methyl)-2H-chromenes: Synthesis and Cytotoxic Activity of 6-(trihalomethyl)-spiro[chromeno(thia)pyrrolizidine-11,3'-indolin]-2'-ones

Unveiling the high reactivity of experimental pseudodiradical azomethine ylides within molecular electron density theory

“…Azomethine ylides (AYs) are a relevant class of TACs participating in 32CA reactions exhibiting the most universal protocol for the preparation of the pyrrolidine and the oxazolidine molecular segments (Scheme 1). 6…”

Diastereoselective Synthesis of Dispiro[Imidazothiazolotriazine-Pyrrolidin-Oxindoles] and Their Isomerization Pathways in Basic Medium

“…A convenient and effective method for the synthesis of spirooxindoles is the [3+2] cycloaddition reaction of azomethine ylides to unsaturated compounds [14][15][16][17][18][19][20][21][22][23][24][25][26][27]. Such reactions often proceed with high diastereoselectivity and allow to obtain products with a certain relative configuration, while other isomers remain unavailable.…”

Green and Efficient Construction of Chromeno[3,4-c]pyrrole Core via Barton–Zard Reaction from 3-Nitro-2H-chromenes and Ethyl Isocyanoacetate

“…The introduction of a trifluoromethyl group into a drug molecule often leads to an increase in its physiological activity because of improvements to the transport characteristics of the drug and an increase in its metabolic stability [ 35 , 36 ]. We have recently developed methods for the synthesis of trifluoromethyl-substituted chromenopyrroli(zi)dines with pronounced cytotoxic activity against HeLa and RD cancer cells [ 37 , 38 , 39 ]. In this work, we report an eco-friendly and efficient approach to the synthesis of 2,4-dihydrochromeno[3,4- c ]pyrroles 12 from 2-mono- and 2,2-disubsituted 3-nitrochromenes 10 and ethyl isocyanoacetate 11 via the Barton–Zard reaction ( Scheme 1 ).…”