Tryptamine Designer Drugs

doi:10.1002/9781118105955.ch11

Medical Toxicology of Drug Abuse 2012

DOI: 10.1002/9781118105955.ch11

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Tryptamine Designer Drugs

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Cited by 11 publications

References 29 publications

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Palladium(II)‐Catalyzed C3‐Selective Friedel–Crafts Reaction of Indoles with Aziridines

Yin

Hyland

2016

Asian J Org Chem

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The [PdCl 2 (MeCN) 2 ]-catalyzed C3-selective Friedel-Crafts reactiono f2 ,2-disubstituted and 2-aryl-N-tosylaziridines with indoles is reported. For the 2,2-disubstituted substrates, [PdCl 2 (MeCN) 2 ]a lone, without any ancillary ligands, is an efficient catalyst for the ring-opening reaction. The presence of 1,4-benzoquinone as an additive was found to en-hance the ring-opening reactiono ft he less-reactive 2-arylaziridines. This reaction displayed ab road substrate scope with respect to the indole substrate and is operationally simple.F inally,w hen 1,3-dimethylindole was employed as as ubstrate, the de-aromatized pyrroloindoline product was obtained in high yield and good diastereoselectivity.[a] J.

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Palladium(II)‐Catalyzed C3‐Selective Friedel–Crafts Reaction of Indoles with Aziridines

Yin

Hyland

2016

Asian J Org Chem

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

Devi

Singh

Mahiya

et al. 2016

Bulletin Korean Chem Soc

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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.

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One‐Pot Aminoethylation of Indoles/Pyrroles with Alkynes and Sulfonyl Azides

Rajasekar

Yadagiri

Anbarasan

2015

Chemistry A European J

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A general and efficient one-pot aminoethylation of substituted indoles/pyrroles was accomplished for the synthesis of various tryptamine derivatives employing a combination of alkynes and sulfonyl azides as readily accessible aminoethylating agents. The reaction features a successful integration of copper-catalyzed alkyne and azide cycloaddition to N-sulfonyl-1,2,3-triazole, rhodium-catalyzed selective insertion of α-iminocarbenes onto the C3-H bond of indoles, and reduction of the resultant enamides to tryptamine derivatives employing either NaCNBH3 or palladium catalyst, in one-pot. The reaction also showed excellent functional-group tolerance and allowed the synthesis of various substituted tryptamines in good to excellent yield. This transformation constitutes a one-pot formal regioselective functionalization of terminal alkynes. Utility of the synthesized tryptamine was further demonstrated in the synthesis of dihydro-β-carboline and tryptoline.

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Tryptamine Designer Drugs

Cited by 11 publications

References 29 publications

Palladium(II)‐Catalyzed C3‐Selective Friedel–Crafts Reaction of Indoles with Aziridines

Palladium(II)‐Catalyzed C3‐Selective Friedel–Crafts Reaction of Indoles with Aziridines

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

One‐Pot Aminoethylation of Indoles/Pyrroles with Alkynes and Sulfonyl Azides

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