Jeminejs, Andris published the artcileApplication of Azide-Tetrazole Tautomerism and Arylsulfanyl Group Dance in the Synthesis of Thiosubstituted Tetrazoloquinazolines, Synthetic Route of 4410-99-5, the publication is Synthesis (2021), 53(8), 1443-1456, database is CAplus.
Nucleophilic aromatic substitution reaction between 4-arylthio-2-chloroquinazolines I (Ar = C6H5, 4-BrC6H4, 4-FC6H4, 4-ClC6H4, 4-CH3C6H4) and NaN3 takes place with an unusual sulfanyl group dance and leads to the formation of 5-(arylthio)tetrazolo[1,5-c]-quinazolines II, 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 III (R1 = cyclopentyl, C6H5, CH2C6H5, etc.), the structure of which has been proved by X-ray crystallog. 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 IV (R2 = C6H5, cyclopropyl, Bu, etc.).
Synthesis published new progress about 4410-99-5. 4410-99-5 belongs to alcohols-buliding-blocks, auxiliary class Thiol,Benzene, name is 2-Phenylethanethiol, and the molecular formula is C8H10S, Synthetic Route of 4410-99-5.
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