SYNTHESIS OF 1,2,3,9a-TETRAHYDRO-9H-IMIDAZO[1,2-<i>a</i>]INDOLE-2-THIONE AND 1,5,6,10b-TETRAHYDROIMIDAZO[2,1-<i>a</i>]ISOQUINOLINE-2(3H)-THIONE DERIVATIVES

Authors

  • E. Valaitytė Department of Organic Chemistry, Kaunas University of Technology, LT-3028 Kaunas
  • V. Martynaitis Department of Organic Chemistry, Kaunas University of Technology, LT-3028 Kaunas
  • A. Šačkus Department of Organic Chemistry, Kaunas University of Technology, LT-3028 Kaunas

Keywords:

imidazo[1, 2-a]indole, imidazo[2, 1-a]isoquinoline, lactam, Lawesson’s reagent, thionation

Abstract

Thionation of 1,2,3,9a-tetrahydro-9H-imidazo[1,2-a]indol-2-one derivative with Lawesson’s reagent in boiling toluene afforded  1,2,3,9a-tetrahydro-9H-imidazo[1,2-a]indol-2-thione derivative. Alkylation of the latter with ethyl iodide in DMF in the presence of a strong base gave 2-ethylthio-9,9,9a-trimethyl-9,9a-dihydro-3H-imidazo[1,2-a]indole. 1,5,6,10b-Tetrahydro-imidazo[2,1-a]isoquinolin-2(3H)-thiones were synthesized by thionation of the corresponding carbonyl substrates.

How to Cite
Valaitytė,  E.; Martynaitis, V.; Šačkus, A.  Chem. Heterocycl. Compd. 2004, 40, 1465. [Khim. Geterotsikl. Soedin. 2004, 1695.]

For this article in the English edition, see DOI 10.1007/s10593-005-0069-8

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Published

2023-12-18

Issue

No. 11 (2004)

Section

Original Papers