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Chemistry of Heterocyclic Compounds

, Volume 54, Issue 8, pp 773–779 | Cite as

Convenient synthetic path to ethyl 1-aryl-5-formyl-1H-1,2,3-triazole-4-carboxylates and 1-aryl-1,5-dihydro-4H-[1,2,3]triazolo[4,5-d]pyridazin-4-ones

  • Nazariy T. Pokhodylo
  • Olga Ya. Shyyka
  • Mykola D. Obushak
Article

A convenient method for selective synthesis of ethyl 1-aryl-5-formyl-1H-1,2,3-triazole-4-carboxylates and 1-aryl-1,5-dihydro-4H-[1,2,3]-triazolo[4,5-d]pyridazin-4-ones has been developed. New ethyl 1-aryl-5-(diethoxymethyl)-1H-1,2,3-triazole-4-carboxylates were prepared by the reaction of different aryl azides and ethyl 4,4-diethoxy-3-oxobutanoate and readily converted into ethyl 1-aryl-5-formyl-1H-1,2,3-triazole-4-carboxylates in high overall yields. Such aldehydes were found to be reactive in several condensation reactions. Reaction of ethyl 1-aryl-5-formyl-1H-1,2,3-triazole-4-carboxylates and hydrazine provided 1-aryl-1,5-dihydro-4H-[1,2,3]triazolo[4,5-d]-pyridazin-4-ones in excellent yields.

Keywords

aryl azide ethyl 4,4-diethoxy-3-oxobutanoate 1H-1,2,3-triazole [1,2,3]triazolo[4,5-d]pyridazine base-promoted cyclocondensation 

Notes

The authors are grateful to the Ministry of Education and Science of Ukraine for financial support (project 0116U008067).

The authors thank Dr. Yuriy Slyvka (Department of Inorganic Chemistry, Ivan Franko National University of Lviv) for X-ray crystallographic analysis.

Supplementary material

10593_2018_2348_MOESM1_ESM.pdf (487 kb)
ESM 1 (PDF 486 kb)

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Nazariy T. Pokhodylo
    • 1
  • Olga Ya. Shyyka
    • 1
  • Mykola D. Obushak
    • 1
  1. 1.Department of Organic ChemistryIvan Franko National University of LvivLvivUkraine

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