Synthesis of 1H-1,2,3-triazole-4-carbonitriles as building blocks for promising 2-(triazol-4-yl)-thieno[2,3-d]pyrimidine drug candidates

Abstract

A new synthetic route leading to functionalized 1H-1,2,3-triazole-4-carbonitriles has been developed. A set of 1-aryl-5-methyl-1H-1,2,3-triazole-4-carbonitriles was obtained in high yields from readily available starting 1H-1,2,3-triazole-4-carboxylic acids via several synthetic protocols. Synthesized 1H-1,2,3-triazole-4-carbonitriles were examined as promising precursors in the simple and efficient method for the preparation of the 2-triazol-4-yl-thieno[2,3-d]pyrimidines. Such an approach allows creating broad combinatorial libraries for anticancer drug discovery.

Graphical Abstract

Keywords:

• 1H-1,2,3-triazole-4-carbonitriles
• 2-triazol-4-yl-thieno[2,3-d]pyrimidines
• 1,2,3-triazole
• Gewald aminothiophene

Acknowledgements

The authors thank Dr Evgeny Goreshnik (Department of Inorganic Chemistry and Technology, Jozef Stefan Institute) and Dr Yuriy Slyvka (Department of Inorganic Chemistry, Ivan Franko National University of Lviv) for X-ray crystallographic analysis.

Additional information

Funding

The authors thank the Ministry of Education and Science of Ukraine for financial support of this project [Grant No 0121U107777].