Regioselective and Diastereoselective Construction of Diverse Dispiro-Indanone-Fluorenone-Oxindole Motifs.

ABSTRACT

A convenient synthetic protocol for regioselective and diastereoselective construction of complex dispiro-indanone-fluorenone-oxindole motifs was developed by the base-promoted annulation reaction of bindone and MBH carbonates of isatins by adjusting reaction conditions. DABCO promoted the annulation reaction of bindone and MBH carbonates of isatins in DCM at room temperature, affording dispiro[indene-2,4'-fluorene-1',3″-indoline] derivatives in good yields and with high diastereoselectivity. Triethylamine promoted the annulation reaction of two molecular 1,3-indanediones and MBH esters of isatins in ethanol at elevated temperature and selectively gave dispiro[indene-2,4'-fluorene-3',3″-indolines] in moderate yields. However, triethylamine promoted the annulation reaction of excess 1,3-indanediones and MBH esters of isatins in refluxing ethanol, affording dispiro[indene-2,4'-fluorene-3',3″-indolines] with the Z-isomer as the major product and the E-isomer as the minor product.