Azido–tetrazole tautomerism of pyrano[3,4-c]pyridine derivatives


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Abstract

Treatment of N-aryl-8-hydrazinylpyrano[3,4-c]pyridine-5-carbonitriles with sodium nitrite in acetic acid afforded the corresponding 8-azido derivatives existing in solution as equilibrium mixtures with cyclic tetrazole tautomer whose fraction attains 48%. Lower solvent polarity and elevated temperature favor increased fraction of the azido tautomer.

About the authors

E. G. Paronikyan

Mndzhoyan Institute of Fine Organic Chemistry, Scientific Technological Center of Organic and Pharmaceutical Chemistry

Email: Shdashyan@gmail.com
Armenia, pr. Azatutyan 26, Yerevan, 0014

Sh. Sh. Dashyan

Mndzhoyan Institute of Fine Organic Chemistry, Scientific Technological Center of Organic and Pharmaceutical Chemistry

Author for correspondence.
Email: Shdashyan@gmail.com
Armenia, pr. Azatutyan 26, Yerevan, 0014

N. S. Minasyan

Molecular Structure Research Center, Scientific Technological Center of Organic and Pharmaceutical Chemistry

Email: Shdashyan@gmail.com
Armenia, pr. Azatutyan 26, Yerevan, 0014

G. M. Stepanyan

Mndzhoyan Institute of Fine Organic Chemistry, Scientific Technological Center of Organic and Pharmaceutical Chemistry

Email: Shdashyan@gmail.com
Armenia, pr. Azatutyan 26, Yerevan, 0014

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