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On the reaction of indole-3-carbaldehyde with cyanothioacetamide: an unexpected approach to indolyl-substituted pyridines and thieno[2,3-b]pyridines
* 1, 2, 3 , 2, 4
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  Lugansk State Medical University, 1-g 50 years of Lugansk Defence, Lugansk 91045, Russia


The reaction of cyanothioacetamide with indole-3-carbaldehyde in the presence of КОН surprisingly leads to potassium 6-amino-3,5-dicyano-4-(1Н-indol-3-yl)pyridine-2-thiolate in good yield. The mechanism is discussed. Upon treatment with alkylating agents, the thiolate gave new 2-(alkylthio)pyridines and thienopyridines bearing 3-indolyl moiety.

Keywords: cyanothioacetamide, indole-3-carbaldehyde, Michael reaction, Thorpe-Ziegler cyclization, thienopyridines