The aminometylation of 4-(alkylthio)-6-amino-2-oxo(thioxo)-1,2-dihydropyridine-3,5-dicarbonitriles

Ekaterina Khrapova; Natalya Ryzhkova; Victor Dotsenko; Nicolai Aksenov

doi:10.3390/ecsoc-24-08401

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SYNTHESIS OF BENZO[b]CARBAZOLS BY TANDEM Au(I)-CATALYZED CYCLIZATION/MIGRATION/CYCLIZATION

The aminometylation of 4-(alkylthio)-6-amino-2-oxo(thioxo)-1,2-dihydropyridine-3,5-dicarbonitriles

Ekaterina A. Khrapova

¹,

Natalya A. Ryzhkova

¹,

Victor V Dotsenko

^{*

2, 3, 4},

Nicolai Aksenov

⁴

¹ Kuban State University
² Department of Organic Chemistry and Technologies, Kuban State University, 149 Stavropolskaya Str., 350040 Krasnodar, Russia
³ ChemEx Lab, Vladimir Dal’ Lugansk National University
⁴ North Caucasus Federal University

Published: 14 November 2020 by MDPI in The 24th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-24-08401

Abstract:

Easily available 2-(bis(alkylthio)methylene)malononitriles react with cyanoacetamide or cyanothioacetamide to give 4-(alkylthio)-6-amino-2-oxo(thioxo)-1,2-dihydropyridine-3,5-dicarbonitriles. Upon treatment with primary amines and/or HCHO, the compounds undergo heterocyclization to afford new pyrido[1,2-а][1,3,5]triazines or ring-condensed 1,3,5,7-tetrazocine derivatives.

Keywords: 6-aminopyridin-2-ones, 2-thioxopyridines, Mannich reaction, aminomethylation, heterocyclization, 1,3,5-triazines, tetrazocines

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