Nucleophile-nucleofuge duality of azide and arylthiolate groups in the synthesis of quinazoline and tetrazoloquinazoline derivatives was written by Jeminejs, Andris;Novosjolova, Irina;Bizdena, Erika;Turks, Maris. And the article was included in Organic & Biomolecular Chemistry in 2021.Electric Literature of C12H20O6 This article mentions the following:
5-Arylthio-tetrazolo[1,5-c]quinazolines (tautomers of 2-arylthio-4-azido-quinazolines) underwent facile nucleophilic aromatic substitution reactions with amines, alcs. and alkylthiols. This, combined with the recently reported arylsulfanyl group dance, provides straightforward access to 4-azido-2-N-, O-, S-substituted quinazolines and/or their tetrazolo tautomers from com. available 2,4-dichloroquinazoline. The azidoazomethine-tetrazole tautomeric equilibrium and the electron-withdrawing character of the fused tetrazolo system plays a central role in the developed transformations. 5-Amino-substituted tetrazolo[1,5-c]quinazolines underwent media-controlled tautomeric equilibrium, which permits them to demonstrate the reactivity traditionally associated with the azido substituent. Furthermore, a method for 5-O-substitited tetrazolo[1,5-a]quinazolines from 2,4-diazidoquinazoline was developed during the structural elucidation of the substitution products. The developed methodol. will facilitate medicinal chem. investigations into quinazoline derivatives and the discovered fluorescent properties of some of the products (e.g., 4-(4-phenyl-1H-1,2,3-triazol-1-yl)-2-(4-methylpiperazin-1-yl)quinazoline: λem. = 461 nm, ΦDCM = 0.89) could serve as a starting point for their further applications in anal. and materials science. In the experiment, the researchers used many compounds, for example, (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5Electric Literature of C12H20O6).
(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5) belongs to tetrahydrofuran derivatives. Tetrahydrofurans and furans are important oxygen-containing heterocycles that often exhibit interesting properties for biological applications or applications in the cosmetic industry. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes. It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.Electric Literature of C12H20O6
Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem