Related Products of 27996-86-7,Some common heterocyclic compound, 27996-86-7, name is 4-[1,2,4]Triazol-1-yl-benzaldehyde, molecular formula is C9H7N3O, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
General procedure: The general procedure for the synthesis of the N-heterocycles using SnAP reagents was as follows. To a solution of the aminotributylstannane-SnAP reagent (0.50 mmol, 1.00 equiv.) in CH2Cl2 (2.5 ml) was added the corresponding aldehyde (0.50 mmol, 1.00 equiv.) and molecular sieve (MS) 4A (50 mg) under an inertat mosphere at r.t. The reaction mixture was stirred for two hours and filtered through a layer of Celite (0.3 cm), rinsing with CH2Cl2. The filtrate was concentrated under reduced pressure to afford the imine. Separately, anhydrous Cu(OTf)2 (0.50 mmol, 1.00 equiv.) was added to as olution of 2,6-lutidine (0.50 mmol, 1.00 equiv.) in HFIP (2.0 ml) in a dry Schlenk flask and stirred at r.t. for one hour, during which a homogeneous suspension formed. A solution of the imine (0.50 mmol, 1.00 equiv.) in dry CH2Cl2 (8.0 ml) was added in one portion and the resulting mixture was allowed to stir at r.t. for 12 hours (unoptimized reaction time). The reaction was quenched at r.t. with a mixture ofsaturated aqueous NaHCO3 (4 ml) and 10% aqueous NH4OH (2 ml). The mixturewas stirred vigorously for 15 minutes, the layers were separated and the aqueous layer was extracted with CH2Cl2 (3 × 5 ml). The combined organic layers were washed with H2O (3 ×5 ml) and brine (10 ml), dried over Na2SO4, filtered, concentrated and purified by flash column chromatography on silica gel using a precolumn of KF (3 cm).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-[1,2,4]Triazol-1-yl-benzaldehyde, its application will become more common.
Reference:
Article; Vo, Cam-Van T.; Luescher, Michael U.; Bode, Jeffrey W.; Nature Chemistry; vol. 6; 4; (2014); p. 310 – 314;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics