- Novel N1-(benzyl)cinnamamidine derived NR2B subtype-selective NMDA receptor antagonists.
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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.
- 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
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- Synthesis of aminoisoquinolines via Rh-catalyzed [4 + 2] annulation of benzamidamides with vinylene carbonate
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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.
- Huang, Xin,Xu, Yingying,Li, Jianglian,Lai, Ruizhi,Luo, Yi,Wang, Qiantao,Yang, Zhongzhen,Wu, Yong
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supporting information
p. 3518 - 3521
(2021/06/12)
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- NHC-Catalyzed Enantioselective [3 + 3] Annulation to Construct 5,6-Dihydropyrimidin-4-ones
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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.
- Meng, Di,Xie, Yangxi,Peng, Qiupeng,Wang, Jian
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supporting information
p. 7635 - 7639
(2020/10/09)
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- Nickel(ii) and nickel(0) complexes as precursors of nickel nanoparticles for the catalytic hydrogenation of benzonitrile
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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.
- Rodríguez, Alejandro A.,Gardu?o, Jorge A.,García, Juventino J.
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supporting information
p. 1082 - 1089
(2020/01/31)
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- Multicomponent reactions (MCRs) of arylmethyl bromides, arylamidines and elemental sulfur toward unsymmetric 3,5-diaryl 1,2,4-thiadiazoles
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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.
- Zhou, Zhen,Liu, Miaochang,Sun, Song,Yao, En,Liu, Suqin,Wu, Zhiwen,Yu, Jin-Tao,Jiang, Yan,Cheng, Jiang
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supporting information
p. 2571 - 2573
(2017/06/13)
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- Base-promoted formal [4?+?1+1] annulation of aldehyde, N-benzyl amidine and DMSO toward 2,4,6-triaryl pyrimidines
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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.
- Yuan, Jin,Li, Jingbo,Wang, Bingbing,Sun, Song,Cheng, Jiang
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supporting information
p. 4783 - 4785
(2017/12/01)
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- Copper-Catalyzed Intramolecular C-H Amination: A New Entry to Substituted Xanthine Derivatives
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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..
- Shimizu, Maki,Hayama, Noboru,Kimachi, Tetsutaro,Inamoto, Kiyofumi
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p. 4183 - 4190
(2017/09/12)
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- Sulfated tungstate catalyzed activation of nitriles: addition of amines to nitriles for synthesis of amidines
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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.
- Veer, Sachin D.,Katkar, Kamlesh V.,Akamanchi, Krishnacharya G.
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supporting information
p. 4039 - 4043
(2016/08/18)
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- Investigating Scale-Up and Further Applications of DABAL-Me3 Promoted Amide Synthesis
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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.
- Lee, Darren S.,Amara, Zacharias,Poliakoff, Martyn,Harman, Thomas,Reid, Gary,Rhodes, Barrie,Brough, Steve,McInally, Thomas,Woodward, Simon
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p. 831 - 840
(2015/07/27)
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- Synthesis of secondary amides from N-Substituted amidines by tandem oxidative rearrangement and isocyanate elimination
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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.
- Debnath, Pradip,Baeten, Mattijs,Lefvre, Nicolas,Van Daele, Stijn,Maes, Bert U. W.
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supporting information
p. 197 - 209
(2015/03/03)
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- A novel straightforward synthesis of 2,4,6-triaryl-1,3,5-triazines via copper-catalyzed cyclization of N-benzylbenzamidines
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A novel, straightforward method for the synthesis of 2,4,6-triaryl-1,3,5-triazines via copper-catalyzed cyclization of N-benzylbenzamidines in DMSO has been developed. Compared to other methods, the present protocol has a number of advantages such as - cost-effectiveness, avoidance of aldehydes or alcohols as reaction partners, and easy accessibility of starting materials, making it a highly practical approach to access various 2,4,6-triaryl-1,3,5-triazines.
- Debnath, Pradip,Majumdar
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supporting information
p. 6976 - 6978
(2015/02/19)
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- Trimethylaluminium-mediated reaction of primary carboxamides with amines and indoles: A convenient synthesis of amidines and indole-3-acylimines
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A simple, convenient and general method, exhibiting good functional group tolerance, is described for the synthesis of N- and N,N-disubstituted amidines by the reaction of primary carboxamides with amines mediated by trimethylaluminium (AlMe3).
- Velavan,Sumathi,Balasubramanian
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p. 5806 - 5815
(2014/10/16)
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- HERBICIDAL BIS-NITROGEN-CONTAINING OXO AND SULFONO HETEROCYCLES
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Disclosed are compounds of Formula (1), including all stereoisomers, N-oxides, and salts thereof, (Formula (1)), X is CH or N; Y is C(O) or S(O)2; provided that when Y is S(O)2, then X is CH; A is a radical selected from the group consisting of Formulae (A-1), (A-2), (A-3), (A-4), (A-5), (A-6) and (A-7); and B1, B2, B3, T, R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12 and R13 are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula (1) and methods for controlling undesired vegetation comprising contacting the undesired vegetation or its environment with an effective amount of a compound or a composition of the invention.
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Page/Page column 98
(2012/03/27)
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- Construction of dihydropyrimidine skeleton using 1,2,4-trisubstituted-1,3- diaza-1,3-butadienes
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Construction of a dihydropyrimidine ring was developed that involved the cyclization of 1,3-diaza-1,3-butadienes having an N-protecting group (N-Cbz, N-Boc, N-alkyl, or N-benzyl) with α,β-unsaturated carbonyl compounds such as ethyl acrylate and p-chlorophenyl vinyl ketone. Consequently, 4-dimethylamino-2-phenyl-1,4,5,6-tetrahydropyrimidines were synthesized in good yields. Subsequently, the β-elimination of the dimethylamino group was carried out with MeI or SiO2 to afford various N-protecting-2,5- disubstituted-1,6-dihydropyrimidines in good yields. Remarkably, the use of 4-chlorophenyl vinyl ketone directly provided the dihydropyrimidine without the tetrahydropyrimidine intermediate in excellent yield.
- Cho, Hidetsura,Nishimura, Yoshio,Yasui, Yoshizumi,Yamaguchi, Masahiko
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supporting information; experimental part
p. 1177 - 1179
(2012/03/26)
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- Synthesis of novel 2-phenyl-5-substituted dihydropyrimidines using 2-phenyl-1,3-diaza-1,3-butadienes and electron-deficient olefins
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A novel synthetic method for 2,5-disubstituted dihydropyrimidines was developed. The cyclization of 1,3-diaza-4-dimethylamino-1,3-butadienes having a N-protecting group (N-Boc, N-Cbz, N-n-C4H9, N-Bn or N-Ph) with electron-deficient olefins, such as α,β-unsaturated carbonyl compounds, phenyl vinyl sulfone, and acrylonitrile was studied in detail. The cyclization smoothly proceeded to afford 4-dimethylamino-1,4,5,6- tetrahydropyrimidines or 1,6-dihydropyrimidines in good yields. The isolated 4-dimethylamino-1,4,5,6-tetrahydropyrimidines were converted to 2,5-disubstituted-1,6-dihydropyrimidines through the β-elimination of the dimethylamino group. 2,5-Disubstituted-1,4(6)-dihydropyrimidines were obtained after removal of the N-Boc or N-Cbz group. Independent tautomers of the resulting dihydropyrimidines were observed.
- Nishimura, Yoshio,Yasui, Yoshizumi,Kobayashi, Satoshi,Yamaguchi, Masahiko,Cho, Hidetsura
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experimental part
p. 3342 - 3350
(2012/07/13)
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- HERBICIDAL PYRIMIDONE DERIVATIVES
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Disclosed are compounds of Formula (1), including all stereoisomers, N-oxides, and salts thereof, Formula : (I) X is CH or N; Y is C(O) or S(O)2; provided that when Y is S(O)2, then X is CH; A is a radical selected from the group consisting of Formula : A-1, A-2, A-3, A-4, A-5, A-6, A-7 and B1, B2, B3, T, R1, R2 R3, R4, R5, R6, R7, R8, R9 R10 R11 R12 and R13 are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula (1) and methods for controlling undesired vegetation comprising contacting the undesired vegetation or its environment with an effective amount of a compound or a composition of the invention.
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Page/Page column 83
(2011/04/18)
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- N-Substituted Glycine Derivatives: Prolyl Hydroxylase Inhibitors
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The invention described herein relates to certain pyrimidinedione N-substituted glycine derivatives of formula (I) which are antagonists of HIF prolyl hydroxylases and are useful for treating diseases benefiting from the inhibition of this enzyme, anemia being one example.
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Page/Page column 7-8
(2008/12/06)
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- Orally efficacious NR2B-selective NMDA receptor antagonists
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A novel series of benzamidines was synthesized and shown to exhibit NR2B-subtype selective NMDA antagonist activity. Compound 31 is orally active in a carrageenan-induced rat hyperalgesia model of pain and shows no motor coordination side effects.
- Claiborne, Christopher F.,McCauley, John A.,Libby, Brian E.,Curtis, Neil R.,Diggle, Helen J.,Kulagowski, Janusz J.,Michelson, Stuart R.,Anderson, Kenneth D.,Claremon, David A.,Freidinger, Roger M.,Bednar, Rodney A.,Mosser, Scott D.,Gaul, Stanley L.,Connolly, Thomas M.,Condra, Cindra L.,Bednar, Bohumil,Stump, Gary L.,Lynch, Joseph J.,Macaulay, Alison,Wafford, Keith A.,Koblan, Kenneth S.,Liverton, Nigel J.
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p. 697 - 700
(2007/10/03)
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- 1,2-Dihydro-1,3,5-triazines from 1,3-diaza-1,3-butadienes
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The 4-aryl-1-(4-methylphenyl)-2-phenyl- and 1-benzyl-2,4-diphenyl-1,3- diaza-1,3-butadienes are nearly quantitatively transformed into the corresponding 1,3,5-triazines when allowed to stand at room temperature in benzene solution. The mechanism of the reaction is discussed.
- Rossi, Elisabetta,Abbiati, Giorgio,Nava, Donatella
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p. 1401 - 1407
(2007/10/03)
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- A New Regioselective Synthesis of 1,2,5-Trisubstituted 1H-Imidazoles and Its Application to the Development of Eprosartan
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A new method is presented for the preparation of 1,2-disubstitued-1H-imidazole-5-carboxaldehydes by the reaction of N-monosubstituted amidines with 2-halo-3-alkoxy-2-propenals. The reaction is highly regioselective with ratios of 1,2,5:1,2,4-imidazolecarboxaldehydes ranging from 85:15 to 100: 0. This methodology could be extended with similar results to the synthesis of imidazole-5-nitriles by the reaction of 2-bromo-3-methoxy-2-propenenitrile with N-monosubstituted amidines.
- Shilcrat, Susan C.,Mokhallalati, Mohamed K.,Fortunak, Joseph M. D.,Pridgen, Lendon N.
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p. 8449 - 8454
(2007/10/03)
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