15421-92-8Relevant articles and documents
Novel N1-(benzyl)cinnamamidine derived NR2B subtype-selective NMDA receptor antagonists.
Curtis, Neil R,Diggle, Helen J,Kulagowski, Janusz J,London, Clare,Grimwood, Sarah,Hutson, Peter H,Murray, Fraser,Richards, Pawel,Macaulay, Alison,Wafford, Keith A
, p. 693 - 696 (2003)
Novel (E)-N(1)-(benzyl)cinnamamidines were prepared and evaluated as NR2B subtype NMDA receptor ligands. Excellent affinity was achieved by appropriate substitution of either phenyl ring. The 2-methoxybenzyl compound 1h had approximately 1,000-fold lower IC(50) in NR2B than NR2A-containing cells. Replacement of the styryl unit by 2-naphthyl was well tolerated.
Synthesis of aminoisoquinolines via Rh-catalyzed [4 + 2] annulation of benzamidamides with vinylene carbonate
Huang, Xin,Xu, Yingying,Li, Jianglian,Lai, Ruizhi,Luo, Yi,Wang, Qiantao,Yang, Zhongzhen,Wu, Yong
supporting information, p. 3518 - 3521 (2021/06/12)
A new strategy is developed for the synthesis of 1-aminoisoquinoline derivatives. This Rh(III)-catalyzed [4 + 2] annulation reaction employs benzamidines as efficient directing groups and the vinylene carbonate as an acetylene surrogate. Additionally, the reaction features broad substrate scopes and good yields, only producing carbonate anion as byproduct.
NHC-Catalyzed Enantioselective [3 + 3] Annulation to Construct 5,6-Dihydropyrimidin-4-ones
Meng, Di,Xie, Yangxi,Peng, Qiupeng,Wang, Jian
supporting information, p. 7635 - 7639 (2020/10/09)
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.
Nickel(ii) and nickel(0) complexes as precursors of nickel nanoparticles for the catalytic hydrogenation of benzonitrile
Rodríguez, Alejandro A.,Gardu?o, Jorge A.,García, Juventino J.
supporting information, p. 1082 - 1089 (2020/01/31)
The use of the nickel(ii) complex [(TEEDA)NiCl2] (1; TEEDA= N,N,N′,N′-tetraethyl-ethylendiamine) and nickel(0) complex [Ni(COD)2] (5) as pre-catalysts in the additive-free catalytic hydrogenation of benzonitrile (BN) is reported. In the presence of 1 (1 mol%), BN was hydrogenated under relatively mild reaction conditions (100 °C, 120 psi H2, 72 h) to the corresponding secondary imine, N-benzylidenebenzylamine (BBA), in very good yield (83%). As a counterpart, 5 (1 mol%) selectively hydrogenated BN to benzylamine (BA) in excellent yield (96%) under similar reaction conditions (80 °C, 120 psi H2, 24 h). In both cases, nickel nanoparticles (Ni-NPs) were identified as the catalytically active species. These Ni-NPs were formed in situ from 1 and 5 without external additives or additional stabilizers. The use of complex 5 was extended to the hydrogenation of different (hetero) aromatic and aliphatic nitriles.
Multicomponent reactions (MCRs) of arylmethyl bromides, arylamidines and elemental sulfur toward unsymmetric 3,5-diaryl 1,2,4-thiadiazoles
Zhou, Zhen,Liu, Miaochang,Sun, Song,Yao, En,Liu, Suqin,Wu, Zhiwen,Yu, Jin-Tao,Jiang, Yan,Cheng, Jiang
supporting information, p. 2571 - 2573 (2017/06/13)
A base-promoted three-component reaction between arylmethyl bromides, arylamidines and elemental sulfur was developed, leading to unsymmetric 3,5-diaryl-1,2,4-thiadiazoles in moderate to good yields with chemical diversity and complexity. This procedure shows broad substrates scope by employing elemental sulfur and commercially available starting materials under transition-metal free conditions.
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.
Copper-Catalyzed Intramolecular C-H Amination: A New Entry to Substituted Xanthine Derivatives
Shimizu, Maki,Hayama, Noboru,Kimachi, Tetsutaro,Inamoto, Kiyofumi
, p. 4183 - 4190 (2017/09/12)
Catalytic synthesis of xanthines was achieved in the presence of a copper catalyst. The process involves copper-catalyzed intramolecular C-H amination of benzamidines that possess a uracil moiety and produces variously substituted xanthines generally in good to high yields. This work introduces a new, facile approach to polysubstituted xanthine compounds..
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.
Investigating Scale-Up and Further Applications of DABAL-Me3 Promoted Amide Synthesis
Lee, Darren S.,Amara, Zacharias,Poliakoff, Martyn,Harman, Thomas,Reid, Gary,Rhodes, Barrie,Brough, Steve,McInally, Thomas,Woodward, Simon
, p. 831 - 840 (2015/07/27)
Methods for the batch scale up of DABAL-Me3 promoted direct ester to amide synthesis have been demonstrated at 10-100 g scales using a tert-amide model compound. Procedures for 20 g scale couplings in standard laboratory glassware and up to 0.1 kg in industry-standard jacketed glass reactors in near quantitative yields are given. A derivative of the anticancer agent Imatinib (Gleevec) has been synthesized on a 26 g scale (98% yield, >98% purity) establishing DABAL-Me3 as a potential alternative for the synthesis of amides in API scale preparations. Continuous flow methodology provides a method for larger scales (productivities of >50 g h-1). In addition, nitriles were coupled to primary amines and hydrazines with DABAL-Me3, resulting in the clean formation of free amidines (16 examples) and amidrazones.
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.
