SYNTHESIS OF 3,9,9,9a-TETRAMETHYL-1,2,3,9a-TETRAHYDRO-9H-IMIDAZO[1,2-<i>a</i>]INDOL-2-ONES BY REACTION OF 2,3,3-TRIMETHYL-3H-INDOLE WITH 2-BROMOPROPIONAMIDES

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:

2-bromopropionamide, imidazo[1, 2-a]indole, spiro[2H-indole-2, 3'-[3H]naphtho-[2, 1-b]pyran], 2, 3, 3-trimethyl-3H-indole

Abstract

Alkylation of 2,3,3-trimethyl-3H-indole with 2-bromopropionamide and the subsequent treatment of the formed 1-(1-carbamoylethyl)-2,3,3-trimethyl-3H-indolium bromide with a base afforded 3,9,9,9a-tetramethyl-1,2,3,9a-tetrahydro-9H-imidazo[1,2-a]indol-2-one. Condensation of the 1-(1-carbamoylethyl)-2,3,3-trimethyl-3H-indolium salt with 2-hydroxy-1-naphthaldehyde gave a mixture of diastereomeric 1-(1-carbamoylethyl)spiro[2H-indole-2,3'-[3H]naphtho[2,1-b]-pyrans].

How to Cite
Valaitytė, E.; Martynaitis,  V.; Šačkus, A.  Chem. Heterocycl. Compd. 2004, 40, 1460. [Khim. Geterotsikl. Soedin. 2004, 1690.]

For this article in the English edition, see DOI 10.1007/s10593-005-0067-x

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Published

2023-12-18

Issue

No. 11 (2004)

Section

Original Papers