Lanthanide(III) ion catalyzed reaction of ammonia and nitriles: Synthesis of 2,4,6‐trisubstituted‐s‐triazines

Abstract

Lanthanum and yttrium trifluoromethanesulfonates at 1 mole % concentration, have been found to catalyze a reaction between ammonia and aromatic nitriles to yield symmetrically substituted 2,4,6‐triaryl‐s‐triazines. The generally high yields and relatively mild reaction conditions of this procedure suggest it as an alternative to other aromatic nitrile cyclotrimerization reactions. Of the aliphatic nitriles studied, acetonitrile and cyclopropanecarbonitrile gave good yields of triazine, propionitrile and butyronitrile gave significantly reduced yields of triazines 3b and 3c respectively. Rearrangement of 3a and 3b to alkylated‐4‐aminopyrimidines was observed.

Transition‐Metal‐Mediated/Catalyzed Synthesis of Pyridines, Pyrimidines, and Triazines by [2+2+2] Cycloaddition Reactions

“…In 1988, Sanders and co‐workers reported that yttrium(III) triflate or lanthanum triflate catalyzed ammonia‐assisted nitrile trimerization . In the presence of 1 mol% Y(OTf) 3 , the reaction of a 1 : 1 molar mixture of benzonitrile ( 32 ) and ammonia at 200 °C for 24 h gave the corresponding triazine ( 180 ) quantitively (Scheme ).…”

Self-Assembly and Host-Guest Behaviors of a Supramolecular Helicate Feii 2l3

“…A typical synthesis (Scheme 1) of the subcomponent triamine (3,3',3''-(1,3,5-triazine-2,4,6-triyl) trianiline) follows the procedure below. A solution of 3-aminobenzonitrile (827 mg, 7 mmol) in 30 mL of dichloromethane was stirred in an ice bath to maintain the temperature below -5 o C. Trifluoromethanesulfonic acid (3 ml, 33.3 mmol) was added dropwise and the resulting mixture was stirred under N 2 atmosphere for 16 h. 29 After the reaction, the yellow layer was separated. Distilled water (50 mL) and 2M NaOH solution were added until pH = 13-14 to afford a pale yellow precipitate.…”

Carrier-Free Microspheres of an Anti-Cancer Drug Synthesized via a Sodium Catalyst for Controlled-Release Drug Delivery

“…The traditional route for amino pyrimidine synthesis using guanidine and imine involves complicated procedures and high costs. The oligomerization of nitriles catalyzed by a base and an organic salt has been reported for the synthesis of the amino pyrimidine structure [ 36 , 37 , 38 ]. Sodium methoxide, IrH(CO)(PPh 3 ) 3 , and sodium hydride have been employed as catalysts in this synthesis [ 39 , 40 , 41 , 42 , 43 ].…”