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EFFECT OF INTRAMOLECULAR HYDROGEN-BOND ON THE AZIDE-TETRAZOLE EQUILIBRIUM OF 5-(2'-HYDROXYPHENYL)TETRAZOLO[1,5-A]PYRIMIDINE, 5-(2'-HYDROXYPHENYL)TETRAZOLO[1,5-C]PYRIMIDINE, 5-(2'-HYDROXYPHENYL)TETRAZOLO[1,5-C]QUINAZOLINE, AND 7-(2'-HYDROXYPHENYL)TETRAZOLO[1,5-C]PYRIMIDINE Full article

Journal Russian Chemical Bulletin
ISSN: 1066-5285 , E-ISSN: 1573-9171
Output data Year: 1995, Volume: 44, Number: 8, Pages: 1435-1443 Pages count : 9 DOI: 10.1007/BF00714425
Tags AZIDOPYRIMIDINES; AZIDOQUINAZOLINES; TETRAZOLOPYRIMIDINES; TETRAZOLOQUINAZOLINES; INTRAMOLECULAR HYDROGEN BOND; AZIDE-TETRAZOLE TAUTOMERISM; H-1 NMR; O-17 NMR SPECTRA
Authors Krivopalov V.P. 1 , Mamatyuk V.I. 1 , Nikolaenkova E.B. 1
Affiliations
1 Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrent'eva, 630090, Novosibirsk, Russian Federation

Abstract: The intramolecular hydrogen bond between the phenolic hydroxyl and the pyrimidine nitrogen atom in the title compounds exerts a destabilizing effect on the tetrazole ring and shifts the azide-tetrazole equilibrium toward the azide farm, especially in the case of tetrazolo[c]pyrimidine and -[c]quinazoline. It has been found that the introduction of a methoxy group into the ortho-position of the phenyl fragment stabilizes the tetrazole tautomer more efficiently than introduction of this group into the para-position.
Cite: Krivopalov V.P. , Mamatyuk V.I. , Nikolaenkova E.B.
EFFECT OF INTRAMOLECULAR HYDROGEN-BOND ON THE AZIDE-TETRAZOLE EQUILIBRIUM OF 5-(2'-HYDROXYPHENYL)TETRAZOLO[1,5-A]PYRIMIDINE, 5-(2'-HYDROXYPHENYL)TETRAZOLO[1,5-C]PYRIMIDINE, 5-(2'-HYDROXYPHENYL)TETRAZOLO[1,5-C]QUINAZOLINE, AND 7-(2'-HYDROXYPHENYL)TETRAZOLO[1,5-C]PYRIMIDINE
Russian Chemical Bulletin. 1995. V.44. N8. P.1435-1443. DOI: 10.1007/BF00714425 WOS Scopus РИНЦ
Dates:
Published print: Aug 1, 1995
Identifiers:
Web of science WOS:A1995TG56600013
Scopus 2-s2.0-21844516806
Elibrary 31114441
OpenAlex W2079644387
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