126229-09-2Relevant academic research and scientific papers
Application of Azide-Tetrazole Tautomerism and Arylsulfanyl Group Dance in the Synthesis of Thiosubstituted Tetrazoloquinazolines
Jeminejs, Andris,Goli?kina, Svetlana M.,Novosjolova, Irina,Stepanovs, Dmitrijs,Bizdēna, ērika,Turks, Māris
, p. 1543 - 1556 (2020/11/23)
Nucleophilic aromatic substitution reaction between 4-aryl-thio-2-chloroquinazolines and NaN 3takes 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 cyclo-addition reaction, leading to the 4-alkyl/arylthio-2-(1 H -1,2,3-triazol-1-yl)quinazolines.
