138785-77-0Relevant academic research and scientific papers
Copper-(II) Catalyzed N-Formylation and N-Acylation of Aromatic, Aliphatic, and Heterocyclic Amines and a Preventive Study in the C-N Cross Coupling of Amines with Aryl Halides
Sonawane, Rahul B.,Rasal, Nishant K.,Bhange, Dattatraya S.,Jagtap, Sangeeta V.
, p. 3907 - 3913 (2018/09/12)
A Cu-(II) catalyzed N-formylation and N-acylation of amines with moderate to excellent yields, using N, N-dimethyl formamide (DMF) and N, N-dimethyl acetamide (DMA) as a formyl and acylating sources in the presence of 1,2,4-triazole is reported. This novel, highly efficient and simple protocol shows broad substrate scope for aliphatic, aromatic, and heterocyclic amines. In addition, the conditions to prevent N-formylation and N-acylation impurities in the C?N cross coupling of amines and aryl halides are described typically when DMF and DMA are used as solvents, with various catalysts, ligands, and bases.
Nickel-(II)-Catalyzed N-Formylation and N-Acylation of Amines
Sonawane, Rahul B.,Rasal, Nishant K.,Jagtap, Sangeeta V.
supporting information, p. 2078 - 2081 (2017/04/28)
A highly efficient protocol of Ni(II) metal complex, [Ni(quin)2], catalyzing N-formylation and N-acylation of amines with moderate to excellent yields, using N,N-dimethylformamide and N,N-dimethylacetamide in the presence of imidazole, is described here. The protocol shows broad substrate scope for aliphatic, aromatic, and heterocyclic amines.
A Practical and General Base-Catalyzed Carbonylation of Amines for the Synthesis of N-Formamides
Li, Wanfang,Wu, Xiao-Feng
supporting information, p. 14943 - 14948 (2015/10/19)
A highly practical and general base-catalyzed carbonylation of amines to the corresponding N-formamides has been realized. Cheap inorganic bases, including GroupIA and IIA metal hydroxides, alkoxides, carbonates, and phosphates, were effective catalysts for the transformation. In the presence of 10-40mol% of KOH or K2CO3, various amines were converted into the corresponding N-formamides in good-to-excellent yields using CO as the formylation reagents. Metal-free carbonylation: A simple and practical procedure for the catalytic carbonylation of amines has been developed (see scheme). In the presence of 10-40mol% of KOH or K2CO3, various amines have been converted into the corresponding N-formamides in good-to-excellent yields by using CO as the formylation reagent.
Absolute configurational assignments of secondary amines by CD-sensitive dimeric zinc porphyrin host
Huang, Xuefei,Fujioka, Naoko,Pescitelli, Gennaro,Koehn, Frank E.,Williamson, R. Thomas,Nakanishi, Koji,Berova, Nina
, p. 10320 - 10335 (2007/10/03)
A general chiroptical protocol for determination of absolute configuration of secondary amines including acyclic and cyclic aliphatic amines, aromatic amines, amino acids, and amino alcohols is described. The chiral substrate is linked to the achiral carrier moiety (3-N-Boc-amino-propyl-N-Boc-amino) acetic acid 1 (BocHNCH2CH2CH2BocNCH2COOH), which after deprotection, yields a bidentate conjugate, capable of forming a 1:1 host/guest complex with dimeric zinc porphyrin host 2. As in the cases of primary amines and secondary alcohols reported earlier, the complexation of secondary amine conjugates to porphyrin tweezer host 2 represents a stereodifferentiating process, where the large (L) group at the stereogenic center (assigned on the basis of conformational energies A value) protrudes from the porphyrin binding pocket. This leads to formation of host/guest complexes with a preferred porphyrin helicity that exhibit intense exciton split CD spectra. It was found that the chiral sense of porphyrin twist is clearly controlled by the stereogenic center despite the Z/E conformational complexity around the tertiary amide bond of secondary amine conjugates that has greatly hampered previous configurational assignments. Thus, in cases where there is no ambiguity regarding the relative steric size of substituents, the observed CD couplet can be applied for straightforward assignment of absolute configurations. In addition, to extend the application to more difficult cases a molecular mechanics calculation approach using the Merck Molecular Force Field (MMFFs) was developed; this provides conformational information of host/guest complexes and leads to prediction of preferred porphyrin helicity independent of conformational A values. This chiroptical protocol in combination with molecular modeling represents a general method for configurational assignments of secondary amines.
Catalytic Leuckart-Wallach-type reductive amination of ketones
Kitamura, Masato,Lee, Donghyun,Hayashi, Shinnosuke,Tanaka, Shinji,Yoshimura, Masahiro
, p. 8685 - 8687 (2007/10/03)
A Cp*Rh(III) complex catalyzes reductive amination of ketones using HCOONH4 at 50-70°C to give the corresponding primary amines in high yields. The reaction is clean and operationally simple and proceeds at a lower temperature and with higher chemoselectivity than the original Leuckart-Wallach reaction. The new method has been applied to the synthesis of α-amino acids directly from α-keto acids.
Asymmetric Catalysis, 77. - New Optically Active Pyrazole Derivatives for Enantioselective Catalysis
Brunner, Henri,Scheck, Thomas
, p. 701 - 710 (2007/10/02)
Starting from the amines 3-6 and the dipyrazolopyrazinedione 2, the optically active (pyrazolylmethyl)amines 11-14 have been synthesized.Furthermore, the preparation of the (+)-camphor-derived optically active pyrazole 17 is described.Pyrazoles 11-13 and 17 are introduced as chiral building blocks into the 2-(1-pyrazolyl)pyridines 30-33.The optically active compounds 23-25 are formed from 2-pyridine and 2,6-bispyridine, respectively, and (+)-3-(bromomethyl)pinane.The pyrazole derivatives 27-29 contain (+)-(1-phenylethyl)hydrazine as the optically active component.Key Words: Pyrazoles, optically active / Pyridines, 2--, 2,6-bis-, 2-(1-pyrazolyl)-
