Application of regioselective nucleophilic substitution reactions of 1-hydroxytryptamines to novel and simple syntheses of serotonin (1a), N-methylserotonin (1b), bufotenine (1c), 5-methoxy-N-methyltryptamine (2a), bufobutanoic acid (3a), N-(indol-3-...
The simple total synthesis of the ergot alkaloids, (±)-norchanoclavine-I, (±)-chanoclavine-I, (±)-isochanoclavine-I, and (±)-agroclavine was achieved by a practical and common synthesis method. A new regio-selective oxidation of the Z-methyl group of...
Serotonins were found to produce 3, 4, 5, 6-tetrahydro-7-hydroxy-1H-azepino[5, 4, 3-cd]indoles by simple heating with amines under an oxygen atmosphere. Serotonins also reacted with various aldehydes to provide 3, 4, 5, 6-tetrahydro-7-hydroxy-1H-azep...
A simple four-step synthetic method for 7-iodo-, 7-bromo-and 7-chloroindole was established with high overall yield starting from 2, 3-dihydroindole. Several 7-substituted indoles carrying a carbon side chain and 7-methoxyindole were also synthesized...
The first syntheses of 1-methoxy analogs of ergot alkaloids, (±)-1-methoxy-6, 7-secoagroclavine and (±)1-methoxy-6-nor-6, 7-secoagroclavine, were achieved with good overall yield in only nine steps from 2-nitrotoluene.
A convenient, short synthesis of (±)-6, 7-secoagroclavine is developed having a 36% overall yield, high regio-and stereo-selectivity, and using no protecting groups.
A simple synthetic method for 5H-pyrido[4, 3-b]indole (γ-carboline) derivatives having a methoxycarbonyl group at the 4-position was developed based on 1-hydroxyindole chemistry. By applying the method, various 3-substituted metyl 5H-pyrido[4, 3-b]in...
A novel photochemical ring-contraction reaction of 5-unsubstituted 3, 1-benzoxazepines and their 5-halogeno or carboxyl derivatives to yield 3-formylindoles in an aprotic solvent is reported. This ring contraction was successfully extended to oxazepi...
Metal-catalyzed hydrolyses of clioquinol-glucuronide (CG) and clioquinol-sulfate (CS) in the rabbit body were studied following intravenous injection of Cu (II)- or Fe (III)-gluconic acid complex system 6h after the oral administration of clioquinol ...
The nature of a substituent on the pyrrole ring of 3-indolecarbaldehyde plays a significant role in governing the regioselectivity of metalation. To confirm the structures of the products, varios indoles carrying a carbon side chain at the 4-, 5-, 6-...
