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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
a   Institute 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
a   Institute 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∗
a   Institute 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
b   Latvian Institute of Organic Synthesis, Aizkraukles Str. 21, Riga, 1006, Latvia
,
Ērika Bizdēna
a   Institute 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  ∗
a   Institute 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
› Author AffiliationsThis work is supported by the Central Finance and Contracting Agency of the Republic of Latvia (ERDF 1.1.1.1. activity project No. 1.1.1.1/16/A/131).
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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706568.
  • Supporting Information


Publication History

Received: 14 July 2020

Accepted after revision: 06 October 2020

Article published online:
12 November 2020

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