Selective Construction of Diverse Polycyclic Spirooxindoles via a Three-Component Reaction of Cyclic Mercapto-Substituted ß-Enamino Esters, Isatins, and Cyclic 1,3-Diketones.

The three-component reaction of alkyl 2-(benzo[b][1,4]thiazin-3-ylidene)acetates, isatins, and 1,3-indanedione (1,3-cyclopentanedione) in ethanol in the presence of acetic acid conveniently afforded spiro[indeno[1,2-b]phenothiazine-6,3'-indolines] or spiro[cyclopenta[b]phenothiazine-4,3'-indolines] in good yields and with high diastereoselectivity. More interestingly, a similar three-component reaction with 4-hydroxychromen-2-one resulted in the unexpected polycyclic spiro[benzo[b]chromeno[3',4':5,6]pyrano[2,3-e][1,4]thiazine-7,3'-indolines] in satisfactory yields. A plausible reaction mechanism was rationally proposed for formation of different kinds of the spiro compounds, and the stereochemistries of the various spiro compounds were clearly elucidated.