Formation and reactions of the cyclic tautomers of tryptophans and tryptamines. VII. Hydroxylation of tryptophans and tryptamines.

Regioselective synthesis of thieno[2,3-b]indoles by tandem cyclisation involving sequential sigmatropic rearrangements

“…The sulfide 3a contains a suitably placed alkynyl segment so as to allow the occurrence of a [2,3] sigmatropic rearrangement in the corresponding sulfoxide. The sulfide 3a was subjected to selective oxidation to the corresponding sulfoxide by the slow addition of one equivalent of m-chloroperoxybenzoic acid (m-CPBA) at 0-5 °C in dichloromethane solution over 1 h. After the completion of the reaction the resultant sulfoxide was refluxed in dichloromethane.…”

“…Furo [3,2-b]indoles 1 show analgesic and anti-inflammatory activity. Cyclic tautomers 2 of tryptophan and serotonin are also important molecules. Thienoindole derivatives 3 are potentially biologically active.…”

“…They reported an unusual sulfoxide rearrangement [7][8][9] for the synthesis of benzo [b]thiophene derivatives, and an amine oxide rearrangement 10 to give indole derivatives. These reactions involve [2,3] and [3,3] sigmatropic rearrangements. The sulfoxide rearrangement has been shown to be an excellent method for C-C bond formation as well as for the construction of thiophene rings in fused heterocycles under mild condition in excellent yield.…”

ATP-Binding Cassette Transporter G2 Mediates the Efflux of Phototoxins on the Luminal Membrane of Retinal Capillary Endothelial Cells

“…Ko143 was synthesized according to the procedure developed by Nakagawa et al (9,10). L-Tryptophan was converted into cis-1-isobutyl-7-methoxy-3-methoxycarbonyl-1, 2,3,4-tetrahydro-b-carboline, known as compound A, which was then condensed with Z-Glu(OBu t )-OH (11) in the presence of dicyclohexylcarbodiimide to form the corresponding amide.…”

Catalyst-free domino-Knoevenagel-hetero-Diels–Alder reaction of terminal alkynes in water: an efficient one-step synthesis of indole-annulated thiopyranobenzopyran derivatives

“…[1][2][3][4][5][6][7][8][9][10][11] Some indole derivatives have been found to possess antitumor activity, some cause inflammation and vascication to human skin. [12][13][14][15] Thiopyranoindole-annulated heterocyclic compounds are important due to their biological activity.…”