116204-77-4Relevant academic research and scientific papers
NHC-Catalyzed Enantioselective [3 + 3] Annulation to Construct 5,6-Dihydropyrimidin-4-ones
Meng, Di,Xie, Yangxi,Peng, Qiupeng,Wang, Jian
, p. 7635 - 7639 (2020)
The unprecedented enantioselective NHC-catalyzed [3 + 3] annulation of α-bromoenals with amidines via a dual C-N bond formation is described. The protocol allows a rapid preparation of 5,6-dihydropyrimidinones in acceptable yields with good enantioselectivities.
Base-promoted formal [4?+?1+1] annulation of aldehyde, N-benzyl amidine and DMSO toward 2,4,6-triaryl pyrimidines
Yuan, Jin,Li, Jingbo,Wang, Bingbing,Sun, Song,Cheng, Jiang
supporting information, p. 4783 - 4785 (2017/12/01)
A base-promoted formal [4 + 1+1] annulation of aldehyde, N-benzyl amidine and DMSO was developed, leading to a series of 2,4,6-triaryl pyrimidines in moderate to good yields. Notably, DMSO served as a methine source, which was activated by base rather than either Lewis acid or electrophile. Molecular O2 was the sole eco-friendly oxidant during this procedure.
Sulfated tungstate catalyzed activation of nitriles: addition of amines to nitriles for synthesis of amidines
Veer, Sachin D.,Katkar, Kamlesh V.,Akamanchi, Krishnacharya G.
supporting information, p. 4039 - 4043 (2016/08/18)
An efficient and mild method for the synthesis of amidines by direct nucleophilic addition of amines to nitriles using sulfated tungstate as heterogeneous catalyst is described. Highlight of the method is its applicability for the synthesis of amidines using a wide variety of amines including ammonia as ammonium acetate and nitriles. Catalyst is mildly acidic, stable, easy to prepare and separate from the reaction mass.
Synthesis of secondary amides from N-Substituted amidines by tandem oxidative rearrangement and isocyanate elimination
Debnath, Pradip,Baeten, Mattijs,Lefvre, Nicolas,Van Daele, Stijn,Maes, Bert U. W.
supporting information, p. 197 - 209 (2015/03/03)
In this work an efficient tandem process transforming N-substituted amidines into secondary amides has been described. The process involves N-acylurea formation by reaction of the substrate with bis(acyloxy)(phenyl)-λ3-iodane followed by isocyanate elimination. The periodinane reagents are obtained from the commercially available phenyl-iodine(III) diacetate [PhI(OAc)2, (PIDA)] by ligand exchange with carboxylic acids. The N-substituted amidine substrates are easily synthesized from readily available nitriles. The method is applicable for secondary amide synthesis, based on both aliphatic and (hetero)aromatic amines, including challenging amides consisting of sterically hindered acids and amines. Moreover, the protocol allows one to combine steric bulk with electron deficiency in the target amides (aniline based). Such compounds are difficult to synthesize efficiently based on classical condensation reactions involving carboxylic acids and amines. Overall, the synthetic protocol transforms a nitrile into a secondary amide in both aliphatic and (hetero)aromatic systems.
Reactions of 3-Aryl-5-methyl-1,2,4-oxadiazoles with Benzyl Alcohol and with Benzylamine
Brown, Jonathan W.,Clack, Dennis W.,Wilson, David A.
, p. 117 - 122 (2007/10/02)
When heated with benzyl alcohol, 3-aryl-5-methyl-1,2,4-oxadiazoles afford mainly the aryl nitrile, benzyl acetate, and benzaldehyde.A number of other products, including 1,3,5-triazines, have been identified.Benzylamine and 5-methyl-1,2,4-oxadiazoles similarly give aryl nitrile and N-acetylbenzylamine, but the reaction is slower.However, in mixtures of the alcohol and the amine, the amine reacts the faster.Possible reaction mechanisms are discussed.The methyl group of the oxadiazole was shown to exchange its protons with those of benzyl alcohol more readily than the oxadiazole otherwise reacted with benzyl alcohol.
