140161-21-3Relevant articles and documents
A New One-Pot Three-Component Synthesis of 4-Aryl-6-cycloamino-1,3,5-triazin-2-amines under Microwave Irradiation
Bin Shahari, Muhammad Syafiq,Junaid, Ahmad,Tiekink, Edward R. T.,Dolzhenko, Anton V.
, p. 2457 - 2468 (2021/03/18)
A new method for the fast synthesis of diverse 4-aryl-6-cycloamino-1,3,5-triazin-2-amines was developed. The synthesis is performed under microwave irradiation in a one-pot manner from cyanoguanidine, aromatic aldehydes, and cyclic amines. Their three-component reaction in the presence of hydrochloric acid produced dihydrotriazines, which were then converted (without isolation) into the targeted compounds via aromatic dehydrogenation in the presence of alkali. The reaction tolerated various aromatic aldehydes (including heterocyclic) and cyclic amines. Crystal structures of two representative 4-aryl-6-morpholino-1,3,5-triazin-2-amines were established by X-ray crystallography. The results of preliminary biological screening identified potent antileukemic activity for 6-[3,4-dihydroisoquinolin-2(1 H)-yl]-4-phenyl-1,3,5-triazin-2-amine.
Ruthenium-catalyzed synthesis of tri-substituted 1,3,5-triazines from alcohols and biguanides
Zeng, Ming,Wang, Tao,Cui, Dong-Mei,Zhang, Chen
supporting information, p. 8225 - 8228 (2016/10/11)
An efficient ruthenium-catalyzed synthesis of tri-substituted 1,3,5-triazines from alcohols and biguanides under mild conditions has been developed. The reaction occurred in moderate to good yields and tolerated benzyl alcohol containing functionalities s
Reactions of Alkylbiguanides with Benzoin at the pH of the Biguanide Bases
Schramm, H. W.,Schubert-Zsilavecz, M.,Saracoglu, A. I.,Kratky, Ch.
, p. 1063 - 1074 (2007/10/02)
Alkylbiguanides 2a-e react with benzoin (1) at the pH of the base in different ways. 1 undergoes in presence of 2a, c oxidation to benzoic acid which reacts with the bases 2a, c to yield 4-phenyl-1,3,5-triazinamines 3c, 4c; in presence of 2b 1 is transformed to benzil, which reacts with 2b under rearrangement to yield 1-(4-oxo-5,5-diphenyl-2-imidazolin-2-yl)-3,3-dimethylguanidine (5b).However, the cycloalkylbiguanides 2d, e react in presence of nitrogen as well as oxygen with 1 to yield piperidine-1- (7d), resp. morpholine-4- (7e).The structure of 7e was established by means of an X-ray structure analysis.All proton- and carbon resonances were assigned on the basis of 2-dimensional NMR data.Keywords: Benzoin, reaction with alkylbiguanides; Imidazoles , 1-(4-oxo-5,5-diphenyl-2-imidazolin-2-yl)-3,3,-dimethyl-guanidine>; Triazines ; NMR; X-ray analysis.