Russian Journal of Organic Chemistry

, Volume 46, Issue 7, pp 1060–1065 | Cite as

Synthesis of new carbamate derivatives of indole and their modification

  • A. V. Velikorodov
  • A. K. Kuanchalieva
  • O. L. Titova
Article

Abstract

Oximation of indoles having a methoxycarbonylamino group on C5 and an acyl group on C3 with hydroxylamine hydrochloride in the presence of pyridine gave the corresponding oximes. The reduction of the 3-C=O group with sodium tetrahydridoborate in the presence of sodium hydroxide was accompanied by removal of the methoxycarbonyl group at the pyrrole nitrogen atom with formation of racemic alcohols. 1,4-Addition of 1-(pyridin-3-yl)butane-1,3-dione to dimethyl 1,4-benzoquinone diimine N,N′-dicarboxylate in dioxane in the presence of sodium methoxide, followed by heating in boiling 22% hydrochloric acid, afforded methyl 2-methyl-5-(methoxycarbonylamino)-3-(pyridin-3-ylcarbonyl)-1H-indole-1-carboxylate. 3-(Dimethylamino)-1-(4-methyl-1,2,5-oxadiazol-3-yl)prop-2-en-1-one reacted with N,N′-bis(methoxycarbonyl)- and N,N′-bis(phenylsulfonyl)-1,4-benzoquinone diimines in methylene chloride and acetic acid, respectively, in the presence of BF3 · Et2O to produce indoles having a 1,2,5-oxadiazolylcarbonyl group on C3.

Keywords

Indole Oxime Methoxycarbonyl Phenylsulfonyl Anti Isomerism 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Pleiades Publishing, Ltd. 2010

Authors and Affiliations

  • A. V. Velikorodov
    • 1
  • A. K. Kuanchalieva
    • 1
  • O. L. Titova
    • 1
  1. 1.Astrakhan State UniversityAstrakhanRussia

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