On the reaction of indole-3-carbaldehyde with cyanothioacetamide: an unexpected approach to indolyl-substituted pyridines and thieno[2,3-b]pyridines

Victor Dotsenko; Sergey Krivokolysko

doi:10.3390/ecsoc-21-04802

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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

Victor V. Dotsenko

^{*

1, 2, 3},

Sergey G. Krivokolysko

^{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

Published: 03 November 2017 by MDPI in The 21st International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-21-04802

Abstract:

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

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Victor Dotsenko

Sergey Krivokolysko