The reaction of 5-amino-3-(cyanomethyl)-1H-pyrazol-4-carbonitrile with beta-cycloketols

¹ Kuban State University, 149 Stavropolskaya Str., Krasnodar 350040, Russian Federation
² ChemEx Lab, Vladimir Dal’ Lugansk National University, Lugansk, 91034 Russia.
³ North-Caucasus Federal University, 1 Pushkina St., 355009 Stavropol, Russian Federation
⁴ The Federal State Unitary Enterprise "Institute of Chemical Reagents and High Purity Chemical Substances" of National Research Centre "Kurchatov Institute", 3 Bogorodsky Shaft, Moscow 107076, Russia

Published: 14 November 2018 by MDPI in The 22nd International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-22-05679

Abstract:

The reaction of 5-amino-3- (cyanomethyl) -1H-pyrazole-4-carbonitrile with 3-aryl-2,4-di(ethoxycarbonyl)-5-hydroxy-5-methylcyclohexanones in boiling acetic acid leads to the formation of new 4,5,6,7,8,9-hexahydropyrazolo[1,5-a]quinazolines. The mechanism is discussed. The structure of the products was confirmed by means of ¹Н и ¹³С (DEPTQ) NMR, as well as 2D NMR (NOESY, ¹Н–¹³С HSQC, HMBC).

Keywords: β-cycloketols, aminopyrazole, cyclocondensation, pyrazolo[1,5-a]quinazoline

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