- Reductive Amination Revisited: Reduction of Aldimines with Trichlorosilane Catalyzed by Dimethylformamide─Functional Group Tolerance, Scope, and Limitations
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Aldimines, generated in situ from aliphatic, aromatic, and heteroaromatic aldehydes and aliphatic, aromatic, and heteroaromatic primary or secondary amines, can be reduced with trichlorosilane in the presence of dimethylformamide (DMF) as an organocatalys
- Campbell, Joanna L. P.,Davies, Christopher D.,Ho?ek, Jan,Ko?ovsky, Pavel,Kysilka, Ond?ej,Popov, Kirill K.,Pour, Milan
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p. 920 - 943
(2022/01/27)
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- Design, synthesis and biological evaluation of new 1,3-thiazole derivatives as potential anti-inflammatory agents
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Thiazoles are widely recognized as nuclei of great value for obtaining molecules with various biological activities, including analgesic, anti-inflammatory, anti-HIV, antidiabetic, antitumor and antimicrobial. A library of 26 thiazole derivatives as fragments were designed, synthesized and evaluated for their anti-inflammatory activities. Some screened compounds showed promising results and were found to be potent in the series by inhibiting LPS-induced TNFα and IL-8 release with IC50 values in μM range without cytotoxic activity.
- Modri?, Marina,Bo?i?evi?, Marin,Faraho, Ivan,Bosnar, Martina,?kori?, Irena
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- Sulfated polyborate: A dual catalyst for the reductive amination of aldehydes and ketones by NaBH4
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An efficient, quick, and environment-friendly one-pot reductive amination of aldehydes or ketones was developed. In ethanol at 70 °C, a imination catalyzed by sulfated polyborate and further reduced by sodium borohydride yields various amines. The present method has many significant benefits, including a shorter reaction time, excellent yields, and a hassle-free, straightforward experimental process. The reaction has a wide range of applications due to its flexibility, including secondary amine for reductive amination.
- Ganwir, Prerna,Chaturbhuj, Ganesh
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- Copper-catalyzed one-pot coupling reactions of aldehydes (ketones), tosylhydrazide and 2-amino(benzo)thiazoles: An efficient strategy for the synthesis of N-alkylated (benzo)thiazoles
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An efficient and practical C–N bond formation methodology for the synthesis of N-alkylated (benzo)thiazoles was developed, via the copper-catalyzed one-pot two-step reactions of 2-amino(benzo)thiazoles and aldehydes (ketones) with tosylhydrazide. This cross-coupling reaction proceeded smoothly and tolerated a broad range of functional groups (46 examples). A variety of functionalized N-alkylated (benzo)thiazoles were obtained in moderate to high yields. Notably, gram-scale synthesis of fanetizole (anti-inflammatory drug) was also realized through this protocol.
- Xie, Zengyang,Chen, Ruijiao,Ma, Mingfang,Kong, Lingdong,Liu, Jun,Wang, Cunde
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- Pd-PEPPSI-IPentAn Promoted Deactivated Amination of Aryl Chlorides with Amines under Aerobic Conditions
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We report herein a highly efficient Pd-catalyzed amination by "bulky-yet-flexible" Pd-PEPPSI-IPentAn complexes. The relationship between the N-heterocyclic carbenes (NHCs) structure and catalytic properties was discussed. Sterically hindered (hetero)aryl chlorides and a variety of aliphatic and aromatic amines can be applied in this cross-coupling, which smoothly proceeded to provide desired products. The operationally simple protocol highlights the rapid access to CAr-N bond formation under mild conditions without the exclusion of air and moisture.
- Huang, Fei-Dong,Xu, Chang,Lu, Dong-Dong,Shen, Dong-Sheng,Li, Tian,Liu, Feng-Shou
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p. 9144 - 9155
(2018/07/21)
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- Ligand-free Iron(II)-Catalyzed N-Alkylation of Hindered Secondary Arylamines with Non-activated Secondary and Primary Alcohols via a Carbocationic Pathway
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Secondary benzylic alcohols represent a challenging class of substrates for N-alkylation of amines. Herein, we describe an iron(II)-catalyzed eco-friendly protocol for N-alkylation of secondary arylamines with secondary benzyl alcohols through a carbocationic pathway instead of the known borrowing hydrogen transfer (BHT) approach. Transiently generated carbocations, produced from alcohols via self-condensation, were coupled with arylamines to provide highly functionalized amine products. The scope of this methodology involves N-alkylation of primary, secondary and heterocyclic amines with primary/secondary benzylic, allylic and heterocyclic alcohols, which are common key structures in numerous pharmaceuticals drugs. The method can also be easily adopted for the amination of various natural products. (Figure presented.).
- Nayal, Onkar S.,Thakur, Maheshwar S.,Kumar, Manoranjan,Kumar, Neeraj,Maurya, Sushil K.
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supporting information
p. 730 - 737
(2017/12/26)
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- Direct Reductive Amination of Aldehydes via Environmentally Benign Bentonite-Gold Nanohybrid Catalysis
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An efficient, green and reliable method for the direct reductive amination of aldehydes was developed using an environmentally benign bentonite-gold nanohybrid catalyst. Use of this heterogeneous catalyst affords a variety of secondary amines in excellent yield under ambient reaction conditions in the presence of phenyldimethylsilane as mild hydride donor. The catalyst is recyclable, selective and is well applicable for the gram-scale preparation of secondary amines. (Figure presented.).
- Maya,Poulose, Susanna,John, Jubi,Luxmi Varma
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p. 1177 - 1184
(2017/04/11)
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- Synthesis of tertiary arylamines: Lewis acid-catalyzed direct reductive: N -alkylation of secondary amines with ketones through an alternative pathway
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We report herein a highly efficient, tin(ii)/PMHS catalyzed reductive N-alkylation of arylamines with ketones affording tertiary arylamines. A very wide substrate scope was observed for the current catalytic method as all six permutations of ketones/aldehydes/heterocyclic carbonyls and primary/secondary/heterocyclic amines were well tolerated, enabling access to secondary, tertiary and heterocyclic amines. The method is also convenient for the synthesis of N-substituted isoindolinones and phthalazinones via a tandem amination-amidation sequence. Mechanistic investigations revealed a carbocationic pathway instead of an ordinary direct reductive amination pathway.
- Nayal, Onkar S.,Thakur, Maheshwar S.,Bhatt, Vinod,Kumar, Manoranjan,Kumar, Neeraj,Singh, Bikram,Sharma, Upendra
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supporting information
p. 9648 - 9651
(2016/08/04)
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- HETEROCYCLIC COMPOUNDS AS POSITIVE MODULATORS OF METABOTROPIC GLUTAMATE RECEPTOR 2 (MGLU2 receptor)
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The present invention relates to heterocyclic compounds which are positive modulators of metabotropic glutamate receptor. The present invention also relates to the use of these compounds for preparing a pharmaceutical composition and to a method of treati
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Page/Page column 47
(2009/01/20)
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- Synthesis of (hetaryl)alkylamines from the reactions of 2-aminopyrimidine, 2-aminothiazole, and 2-aminothiazoline with benzyl bromide and xylylene dibromides
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Alkylation reactions of 2-aminopyrimidine, 2-aminothiazole, 2-aminothiazoline, and their Cbz-protected derivatives are described. Reactions with benzyl bromide proceed to give monoalkylated products with 2-aminopyrimidine and 2-aminothiazole, but 2-aminot
- Gondi, Sudershan R.,Son, David Y.
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p. 401 - 410
(2008/04/01)
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- Heteroaryl substituted bis-trifluoromethyl carbinols as malonyl-CoA decarboxylase inhibitors
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A series of heteroaryl-substituted bis-trifluoromethyl carbinols were prepared and evaluated as malonyl-CoA decarboxylase (MCD) inhibitors. Some thiazole-based derivatives showed potent in vitro MCD inhibitory activities and significantly increased glucos
- Cheng, Jie-Fei,Mak, Chi Ching,Huang, Yujin,Penuliar, Richard,Nishimoto, Masahiro,Zhang, Lin,Chen, Mi,Wallace, David,Arrhenius, Thomas,Chu, Donald,Yang, Guang,Barbosa, Miguel,Barr, Rick,Dyck, Jason R.B.,Lopaschuk, Gary D.,Nadzan, Alex M.
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p. 3484 - 3488
(2007/10/03)
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- Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures
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Sodium triacetoxyborohydride is presented as a general reducing agent for the reductive amination of aldehydes and ketones. Procedures for using this mild and selective reagent have been developed for a wide variety of substrates. The scope of the reaction includes aliphatic acyclic and cyclic ketones, aliphatic and aromatic aldehydes, and primary and secondary amines including a variety of weakly basic and nonbasic amines. Limitations include reactions with aromatic and unsaturated ketones and some sterically hindered ketones and amines. 1,2-Dichloroethane (DCE) is the preferred reaction solvent, but reactions can also be carried out in tetrahydrofuran (THF) and occasionally in acetonitrile. Acetic acid may be used as catalyst with ketone reactions, but it is generally not needed with aldehydes. The procedure is carried out effectively in the presence of acid sensitive functional groups such as acetals and ketals; it can also be carried out in the presence of reducible functional groups such as C-C multiple bonds and cyano and nitro groups. Reactions are generally faster in DCE than in THF, and in both solvents, reactions are faster in the presence of AcOH. In comparison with other reductive amination procedures such as NaBH3CN/MeOH, borane-pyridine, and catalytic hydrogenation, NaBH(OAc)3 gave consistently higher yields and fewer side products. In the reductive amination of some aldehydes with primary amines where dialkylation is a problem we adopted a stepwise procedure involving imine formation in MeOH followed by reduction with NaBH4.
- Abdel-Magid, Ahmed F.,Carson, Kenneth G.,Harris, Bruce D.,Maryanoff, Cynthia A.,Shah, Rekha D.
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p. 3849 - 3862
(2007/10/03)
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- OBTENTION D'AMINO-2 THIAZOLES-1,3 PAR ACTION D'AMINES PRIMAIRES SUR DES α-HALO β-THIOCYANATO ALCENES
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Action of primary amines on vic-halo-thiocyanato alkenes R1-C(-SCN)=CX-R%&2 affords 2-amino 1,3-thiazoles, the cyclisation taking place with migration of the sulphur atom on the C=C bond; thus 2-cyclohexylamino 5-propyl 1,3-thiazole is obtained
- Giffard, Michel,Cousseau, Jack
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p. 5085 - 5088
(2007/10/02)
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