Novel Synthesis of Tryptamine Derived 4‐Hydroxy‐4‐arylthiazolidine‐2‐thiones and 4‐Arylthiazole‐2(3H)‐thiones by Multicomponent Reactions

Abstract

An efficient one-pot multicomponent synthesis of 3-(2-(1H-indol-3-yl)ethyl)-4-hydroxy-4-arylthiazolidine-2-thione and 3-(2-(1H-indol-3-yl)ethyl)-4-arylthiazole-2(3H)-thione has been developed from a multicomponent reaction of tryptamine, carbon disulfide and phenacyl bromide. This protocol has an advantage such as operational simplicity, short reaction time, and affording good to excellent yields.

Multicomponent Approaches Involving Carbon Disulfide

“…Reaction in ethanol under reflux condition for 3 h led to formation of thiazolidin‐2‐thiones (Scheme 21). [52] Typically, substrates with electron‐rich groups (p‐Me and p‐OMe), formed improved yields than the substrate containing electron‐deficient groups (p‐Br and p‐NO 2 ). Nucleophilic addition, nucleophilic substitution, intramolecular cyclization and elimination of water molecule are the major steps leading to the desired product.…”

Interpol review of controlled substances 2016–2019

“…Tryptamines (see also Mushrooms): 2016 square wave adsorptive stripping voltammetry for determination of tryptamine [ 1181 ]; synthesis of synthesis of 3-(2-(1H-indol-3-yl)ethyl)-4-hydroxy-4-arylthiazolidine-2-thione and 3-(2-(1H-indol-3-yl)ethyl)-4-arylthiazole-2(3H)-thione [ 1182 ]; synthesis of functionalized 3-{1-[2-(1H-indol-3-yl) ethyl]-4,5,6,7-tetra-hydro-1H-indol-3-yl} indolin-2-ones [ 1183 ]; HPLC-DAD method for detecting terpenoid indole alkaloids in different parts and different developmental stages of Catharanthus roseus plants [ 1184 ]; Solid Surface-Room Temperature Phosphorescence (SS-RTP) for direct determination of the concentration of tryptamine in beers [ 1185 ]; RP-HPLC-DAD for determination of the biogenic amines tryptamine, putrescine, histamine, phenylethylamine, tyramine, cadaverine, spermidine and spermine in red and white wines [ 1186 ]; 2017 analytical characterization of 17 DALTs using NMR, GC quadrupole and ion trap (EI/CI) MS, low and high mass accuracy MS/MS, photodiode array detection, and GC solid-state infrared analysis [ 1187 ]; LC-MS method for quantification of Tryptophan [ 1188 ]; characterization of omega-N-methyl-4-hydroxytrypt-amine (norpsilocin, 1) using 1D and 2D NMR spectroscopy and high-resolution mass spectrometry [ 789 ]; detection of 5-fluoro-DALT (5-F-DALT), 7-methyl-DALT (7-Me-DALT), and 5,6-methylenedioxy-DALT (5,6-MD-DALT) using GC-MS, LC-MS/MS and LC-HR-MS/MS [ 1189 ]; GC-MS analysis of 25,296 samples of which 436 were tryptamines; from these 232 (53.21%) were non-regulated (the most delivered non-regulated tryptamine was 4-AcO-DMT) [ 1190 ]; SPE-LC-UV-DAD for determination of tryptamines Ayahuasca, a potent hallucinogenic beverage [ 552 ]; use of tryptamine as a reactive matrix for the analysis of non-polar carbonyl compounds by MALDI-MS [ 1191 ]; UPLC-TQ/MS method for direct determination of biogenic amines tryptamine, putrescine, histamine, phenylethylamine, tyramine, cadaverine, spermine, and spermidine in wine [ 1192 ]; 2018 detection of 5-MeO-2-Me-DALT, 5-MeO-2-Me-ALCHT, 5-MeO-2-Me-DIPT using GC-MS, LC-MSn and LC-HR-MS/MS [ 1193 ]; investigation and comparison of mass fragmentation of 20 phenethylamine/tryptamine standards by means of MALDI/TOFM, GC-EI/MS and LC-ESI/MS [ 877 ]; trends in use of tryptamines-specifically DMT, alpha-methyltryptamine (AMT), and 5-MeO-DIPT (“Foxy”) [ 1194 ];…”