EventsThe 24th International Electronic Conference on Synthetic Organic Chemistry
Event submissions
Published
with-doi10.3390/ecsoc-24-08400
This submission belongs to the session A. General Organic Synthesis of the event The 24th International Electronic Conference on Synthetic Organic Chemistry
Published date
14 Nov, 2020
Citation
Victor V Dotsenko, Tatyana S. Didikina, Elena A. Chigorina, Darya Yu. Lukina, Alexander V. Bespalov, Nicolai A. Aksenov, N-(Thieno[2,3-b]pyridin-3-yl)cyanoacetamides: synthesis and cyclizations, in Proceedings of The 24th International Electronic Conference on Synthetic Organic Chemistry, 15 November–15 December 2020, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-24-08400
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N-(Thieno[2,3-b]pyridin-3-yl)cyanoacetamides: synthesis and cyclizations

Tatyana S. Didikina 1
Elena A. Chigorina 2
Darya Yu. Lukina 1
Alexander V. Bespalov 1
Victor V Dotsenko 3,4,5
Nicolai A. Aksenov 5
1. Kuban State University
2. The Federal State Unitary Enterprise “Institute of Chemical Reagents and High Purity Chemical Substances” of National Research Centre “Kurchatov Institute”, 3 Bogorodsky Val, Moscow, 107076, Russia
3. Department of Organic Chemistry and Technologies, Kuban State University, 149 Stavropolskaya Str., 350040 Krasnodar, Russia
4. ChemEx Lab, Vladimir Dal’ Lugansk National University
5. North Caucasus Federal University
Abstract

A series of N-(thieno[2,3-b]pyridin-3-yl)cyanoacetamides were prepared by reaction of 3-aminothieno[2,3-b]pyridines with 1-cyanoacetyl-3,5-dimethytlpyrazole. Upon treatment with alkali, N-(2-alkoxycarbonylthieno[2,3-b]pyridin-3-yl)cyanoacetamides undergo Camps-type cyclization to give dipyridothiophenes. The relative stability of their tautomers was estimated by quantum chemical calculations. In contrast, cyclization of 3-(2-cyanoacetamido)thieno[2,3-b]pyridine-2-carboxamides lead to the formation of pyrido[3’,2’:4,5]thieno[3,2-d]pyrimidines.

Keywords
heterocyclization
Camps reaction
thienopyridines
cyanoacetylation
Manuscript
GeneralOrganicSynthesis_8400_N_Thieno_2_3_b_pyridin_3_yl_c_original-DONE.pdf
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