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Synthesis of some new fluorine containing 3-dialkylaminomethyl indoles, 3-indolylglyoxamides and tryptamines

Synthese einiger neuer Fluor enthaltender 3-Dialkylaminomethyl-indole, 3-Indolylglyoxamine und Tryptamine

Abstract

Several new 2-(fluoroaryl)-3-dialkylaminomethylindoles, 3-acetyl-2-(fluoroaryl)-indoles, 2-(fluoroaryl)-3-indolylglyoxamides and corresponding tryptamines have been prepared as possible psychopharmacological agents. 2-(Fluoroaryl)-indoles have been synthesized by theFischer indole synthesis. 2-(Fluoroaryl)-indoles on treatment with oxalyl chloride and subsequent reaction with amines, gave 2-(fluoroaryl)-3-indolylglyoxamides. Some of these indolylglyoxamides were reducted with lithium aluminium hydride, to the corresponding tryptamines. 2-(Fluoroaryl)-indoles when subjected toMannich reaction afforded 3-dialkylaminomethyl-2-(fluoroaryl)-indoles. All these new compounds have been characterized by IR spectral studies.

Zusammenfassung

Die Titelverbindungen wurden wegen eventueller psychopharmakologischer Wirksamkeit synthetisiert. 2-(Fluoraryl)-indole wurden nach derFischer schen Indolsynthese hergestellt, 2-(Fluoraryl)-3-indolyl-glyoxamide durch Behandlung mit Oxalylchlorid und Aminen. Reduktion ergab die entsprechenden Tryptamine. Außerdem wurden die 2-(Fluoraryl)-indole mittelsMannich-Reaktion in 3-Dialkylaminomethyl-2-(fluoraryl)-indole übergeführt. Die Infrarotspektren aller neuen Verbindungen wurden untersucht.

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Possible Psychopharmacological Agents, Part XII, Part XI, J. Indian. Chem. Soc.57, 423 (1980).

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Joshi, K.C., Pathak, V.N. & Singh, R.P. Synthesis of some new fluorine containing 3-dialkylaminomethyl indoles, 3-indolylglyoxamides and tryptamines. Monatshefte für Chemie 111, 1343–1350 (1980). https://doi.org/10.1007/BF00903661

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Keywords

  • Indoles
  • Mannich reaction
  • Tryptamines