Efficient construction of diverse spiro[indoline-3,4'-pyrrolo[3,4-b]pyridines] via [3 + 3] cycloaddition of MBH carbonates of isatins with ß-enamino maleimides.

An efficient method to construct unique spiro[indoline-3,4'-pyrrolo[3,4-b]pyridines] was successfully developed via a DABCO promoted formal [3 + 3] cycloaddition reaction of MBH carbonates of isatins with ß-enamino maleimides in acetonitrile at room temperature. This reaction afforded multifunctionalized spiro[indoline-3,4'-pyrrolo[3,4-b]pyridines] and spiro[dipyrrolo[3,4-b:3',4'-e]pyridine-8,3'-indolines] in good yields and with lower diastereoselectivity. The relative configuration of the two diasteromers of the spiro compounds was clearly elucidated by the determination of eight single crystal structures.

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.