Stereoselective synthesis of dialkyl 3-spiroindanedione-1,2,3,3a-tetrahydropyrrolo[1,2-a]quinoline-1,2-dicarboxylates

The 1:1 intermediate generated by the addition of quinoline to dialkyl acetylenedicarboxylates is trapped by 1,3-indanedione to yield dialkyl 3-spiroindanedione-1,2,3,3a-tetrahydropyrrolo[1,2-a]quinoline-1,2-dicarboxylates in good yields. The structures of these products were confirmed by NMR and single-crystal X-ray diffraction studies. (C) 2008 Elsevier Ltd. All rights reserved.