65610-13-1Relevant articles and documents
Preparation of Polyfunctionalized Aromatic Nitriles from Aryl Oxazolines
Hess,Guelen,Alandini,Mourati,Guersoy,Knochel
supporting information, (2021/12/06)
A selective ortho,ortho’-functionalization of readily available aryl oxazolines by two successive magnesiations with sBu2Mg in toluene followed by trapping reactions with electrophiles, such as (hetero)aryl iodides or bromides, iodine, tosyl cyanide, ethyl cyanoformate or allylic bromides (39 examples, 62–99 % yield) is reported. Treatment of these aryl oxazolines with excess oxalyl chloride and catalytic amounts of DMF (50 °C, 4 h) provided the corresponding nitriles (36 examples, 73–99 % yield). Conversions of these nitriles to valuable heterocycles are reported, and a tentative mechanism is proposed.
Further Studies on the Synthesis of Quinazolines from 2-Fluorobenzonitriles
Hynes, John B.,Tomazic, Alenka,Parrish, Christie A.,Fetzer, Oliver S.
, p. 1357 - 1364 (2007/10/02)
Recently, we reported that appropriately substituted 2-fluorobenzonitriles undergo cyclization with guanidine carbonate to afford 2,4-diaminoquinazolines usually in good to excellent yield.This paper describes the preparation of a variety of new 2,4-diaminoquinazolines substituted at positions five or seven.In addition, the reactions of selected 2-fluorobenzonitriles with formamidine acetate or acetamidine acetate were examined.The results obtained demonstrate that the analogous 4-amino- and 2-methyl-4-aminoquinazolines can be prepared by this approach but that yields are considerably lower than when guanidine carbonate is employed as the cyclization reagent.
