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New methods of synthesis, structure and aminomethylation of 4-imino-2-(dicyanomethylene)-3-azaspiro[5.5]undecane1,5-dicarbonitrile
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1
,
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2
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Sergey Krivokolysko
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3
,
Konstantin Frolov
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4
Academic Editor: Julio A. Seijas
Published:
14 November 2021
by MDPI
in The 25th International Electronic Conference on Synthetic Organic Chemistry
session General Organic Synthesis
https://doi.org/10.3390/ecsoc-25-11741
(registering DOI)
Abstract:
Sequential reaction of cyclohexanone with malononitrile and 2-aminopropene-1,1,3-tricarbonitrile in potassium hydroxide or sodium ethylate in ethanol gave 4-imino-2- (dicyanomethylene) -3-azaspiro [5.5] undecane-1, 5-dicarbonitrile ... The latter reacts with primary amines and an excess of formaldehyde to form new derivatives of 2- (dicyanomethylene) -3,7-diazaspiro [bicyclo [3.3.1] non-3-ene-9,1'-cyclohexane] -1,5-dicarbonitrile. ... Contrary to the literature data, the reaction of cyclohexanone with 2-aminopropene-1,1,3-tricarbonitrile in benzene in the presence of piperidine and glacial acetic acid led to the formation of 2,4-diamino-5,6,7,8-tetrahydronaphthalene-1,3-dicarbonitrile
Keywords: cyclohexanone; malononitrile; 2-aminopropene-1,1,3-tricarbonitrile; 2,4-diamino-5,6,7,8-tetrahydronaphthalene-1,3-dicarbonitrile; 4-imino-2-(dicyanomethylene)-3-azaspiro[5.5]undecane-1,5-dicarbonitrile; aminomethylation
