110317-54-9Relevant academic research and scientific papers
Hexahydropyrroloindoles - Attempts to Synthesize 2-Indolyl Thioethers
Droste, Holger,Wieland, Theodor
, p. 901 - 910 (2007/10/02)
The N-tryptamine derivatives 9, 11, 12, and 19 with the functional groups CN, CONH2, CO2H, and CO2Me, respectively, in the α position to the indole ring have been synthesized.Sensitized photooxiation of 9, 12, 19, N-Boc--tryptophan (21), and N-Boc-tryptamine (22) affords the hexahydropyrroloindoles 23-27, in the case of 11 the ring closure occurs at the amine nitrogen to give the ketone 28, N-Boc-homotryptamine (31) yields the hexahydropyridoindole 32, whereas no azetidine formation from 2-(3-indolyl)glycine (36) is observed.The oxi mes 34a and 34 b, intermediates in the synthesis of 36, have been separated chromatographically and characterized NMR spectroscopically as E and Z-isomers, respectively.- Attempts to introduce with cysteine derivatives a thioether group in position 2 of the compounds described above, failed. 21, 22, 26, 27, and N-Boc-2-(3-indolyl)propylamine (43), bearing a methyl group in the α position to the indole ring, and its photooxidation product 44 show only thin-layer chromatographically detectable thioether formation.
