EventsThe 21st International Electronic Conference on Synthetic Organic Chemistry
Event submissions
Published
with-doi10.3390/ecsoc-21-04802
This submission belongs to the session A. General Organic Synthesis of the event The 21st International Electronic Conference on Synthetic Organic Chemistry
Published date
03 Nov, 2017
Citation
Victor V. Dotsenko, Sergey G. Krivokolysko, On the reaction of indole-3-carbaldehyde with cyanothioacetamide: an unexpected approach to indolyl-substituted pyridines and thieno[2,3-b]pyridines, in Proceedings of The 21st International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2017, MDPI: Basel, Switzerland, 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
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
Manuscript
ECOSC 21 2017 indol.pdf
Some new reactions and properties of xanthane hydride
Synthesis of new spiro pyrido[3',2':4,5]thieno[3,2-d]pyrimidines