Diastereoselective Synthesis of Spiro[chromeno-pyrazole-indoline] and Spiro[chromeno-pyrazole-indene] Derivatives

نویسندگان

1 Department of Chemistry, Tarbiat Modares University PO Box 14115-175, Tehran, Iran

2 Department of Chemistry, Tarbiat Modares University PO Box 14115-175, Tehran, Iran

doi
10.22036/org.chem.2025.494540.1369
چکیده

A diastereoselective synthesis of spiro[chromeno-pyrazole-indoline] and spiro[chromeno-pyrazole-indene] derivatives through a three-component reaction of cyclic ketones, pyrazolone derivatives, and isatin or ninhydrin, in the presence of trifluoroacetic acid in EtOH is described. This reaction forms three contiguous stereogenic centers with remarkable diastereoselectivity, one of which is quaternary. The practical applicability of this approach was further illustrated through a gram-scale experiment, and the final product's structure was confirmed via single-crystal X-ray analysis, affirming the successful synthesis of the target compounds.

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