Application of Azide-Tetrazole Tautomerism and Arylsulfanyl Group Dance in the Synthesis of Thiosubstituted Tetrazoloquinazolines

Andris Jeminejs; Svetlana M. Goliškina; Irina Novosjolova; Dmitrijs Stepanovs; Ērika Bizdēna; Māris Turks

doi:10.1055/s-0040-1706568

Synthesis, Table of Contents

Synthesis 2021; 53(08): 1443-1456
DOI: 10.1055/s-0040-1706568

paper

Application of Azide-Tetrazole Tautomerism and Arylsulfanyl Group Dance in the Synthesis of Thiosubstituted Tetrazoloquinazolines

Andris Jeminejs

^aInstitute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, Paula Valdena Str. 3, Riga, 1048, Latvia Email: irina.novosjolova@rtu.lv Email: maris.turks@rtu.lv

,

Svetlana M. Goliškina

^aInstitute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, Paula Valdena Str. 3, Riga, 1048, Latvia Email: irina.novosjolova@rtu.lv Email: maris.turks@rtu.lv

,

Irina Novosjolova∗

^aInstitute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, Paula Valdena Str. 3, Riga, 1048, Latvia Email: irina.novosjolova@rtu.lv Email: maris.turks@rtu.lv

,

Dmitrijs Stepanovs

^bLatvian Institute of Organic Synthesis, Aizkraukles Str. 21, Riga, 1006, Latvia

,

Ērika Bizdēna

^aInstitute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, Paula Valdena Str. 3, Riga, 1048, Latvia Email: irina.novosjolova@rtu.lv Email: maris.turks@rtu.lv

,

Māris Turks ∗

^aInstitute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, Paula Valdena Str. 3, Riga, 1048, Latvia Email: irina.novosjolova@rtu.lv Email: maris.turks@rtu.lv

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Abstract

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Abstract

Nucleophilic aromatic substitution reaction between 4-arylthio-2-chloroquinazolines and NaN₃ takes place with an unusual sulfanyl group dance and leads to the formation of 5-(arylthio)tetrazolo[1,5-c]-quinazolines, which do not form the azide tautomer and do not undergo CuAAC reactions with alkynes. On the other hand, 5-azidotetrazolo[1,5-a]quinazoline (formally described as 2,4-diazidoquinazoline) undergoes regioselective nucleophilic aromatic substitution with thiols at C5 and forms 5-(alkyl/arylthio)tetrazolo[1,5-a]quinazolines, the structure of which has been proved by X-ray crystallography. The latter exist in tautomeric equilibrium with their 2-azidoquinazoline form, which provides possibility for copper-catalyzed azide–alkyne 1,3-dipolar cycloaddition reaction, leading to the 4-alkyl/arylthio-2-(1H-1,2,3-triazol-1-yl)quinazolines.

Key words

quinazolines - nucleophilic aromatic substitution - azide-tetrazole equilibrium - thiols - azides - triazoles

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References

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