80616-00-8Relevant articles and documents
2',3',4',9'-Tetrahydrospiroindol>-2-ones and Their Transformations into 2,3,4,4a,5,6,9,14-Octahydro-4a-hydroxy-1H,8H-pyridodiindole-5-carbonitriles and 5-Substituted 2,3,4,4a,9,14-hexahydro-4a-hydroxy-1H,8H-indolopyrido<1,2-c...
Bobowski, George
, p. 1179 - 1187 (2007/10/02)
The condensation of 1H-indol-3-ethanamine derivatives 1 with 1,2-cyclohexanedione (2) and subsequent transformation of the resulting 2-imino>cyclohexanones (3) into 2',3',4',9'-tetrahydrospiroindol>-2-ones 4 using Pistet-Spengler (1) reaction conditions is described.The reaction of 4 with acrylonitrile gave a mixture of pentacyclic derivatives, 2,3,4,4a,5,6,9,14-octahydro-4a-hydroxy-1H,8H-pyridodiindole-5-carbonitriles 12.Treatment of 4 with alkyl and aryl isocyanates (14) at room temperature gave 5-sub stituted-2,3,4,4a,9,14-hexahydro-4a-hydroxy-1H,8H-indolopyridobenzimidazol-6-(5H)ones 16.Dehydration of 16 gave 5-substituted-2,3,9,14-tetrahydro-1H,8H-indolopyridobenzimidazol-6-(5H)ones (17).Spectral and chemical evidence is presented to confirm structures 4,12,16, and 17.
