US EPA

3740928 

Journal Article 

Synthesis of new carbamate derivatives of indole and their modification 

Velikorodov, AV; Kuanchalieva, AK; Titova, OL 

2010 

1 

Russian Journal of Organic Chemistry
ISSN: 1070-4280
EISSN: 1608-3393 

46 

7 

1060-1065 

English 

10.1134/S107042801007016X 

WOS:000280923200016 

http://link.springer.com/10.1134/S107042801007016X
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Oximation of indoles having a methoxycarbonylamino group on C(5) and an acyl group on C(3) 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 BF(3) center dot Et(2)O to produce indoles having a 1,2,5-oxadiazolylcarbonyl group on C(3).