82740-60-1Relevant articles and documents
Nickel-catalyzed reductive amidation of aryl-triazine ethers
Heravi, Majid M.,Panahi, Farhad,Iranpoor, Nasser
supporting information, p. 1992 - 1995 (2020/02/22)
The reaction of activated phenolic compounds, 2,4,6-triaryloxy-1,3,5-triazine (aryl-triazine ethers), with various isocyanates or carbodiimides in the presence of a nickel pre-catalyst resulted in the synthesis of aryl amides in good to excellent yields.
Quantitative investigation of C-H?π and other intermolecular interactions in a series of crystalline: N -(substituted phenyl)-2-naphthamide derivatives
Shukla, Rahul,Saeed, Aamer,Simpson, Jim,Chopra, Deepak
, p. 5473 - 5491 (2017/09/26)
In this study, we have investigated the nature and characteristics of different intermolecular interactions present in a series of seven N-(substituted phenyl)-2-naphthamides. The seven structures comprise 2-naphthyl ring systems linked by amide bridges to N-bound phenyl 1, or substituted benzene rings 3-7, or in the case of 2, a cyclohexane ring. A common feature of the crystal packing for all but the o-nitro derivative 7 is the presence of a strong intermolecular N-H?O interaction. In the case of 7, the possibility of such an interaction is obviated by the formation of an intramolecular N-H?O hydrogen bond. An additional feature of the crystal packing for 1-6 is the significant roles that C-H?π contacts play in generating three-dimensional networks. In contrast for 7, the intramolecular N-H?O hydrogen bond precludes the formation of molecular chains but the planar nature of this molecule allows significant π?π stacking interactions to stabilize the packing.
Photoinduced, copper-catalyzed alkylation of amides with unactivated secondary alkyl halides at room temperature
Do, Hien-Quang,Bachman, Shoshana,Bissember, Alex C.,Peters, Jonas C.,Fu, Gregory C.
supporting information, p. 2162 - 2167 (2014/03/21)
The development of a mild and general method for the alkylation of amides with relatively unreactive alkyl halides (i.e., poor substrates for S N2 reactions) is an ongoing challenge in organic synthesis. We describe herein a versatile transition-metal-catalyzed approach: in particular, a photoinduced, copper-catalyzed monoalkylation of primary amides. A broad array of alkyl and aryl amides (as well as a lactam and a 2-oxazolidinone) couple with unactivated secondary (and hindered primary) alkyl bromides and iodides using a single set of comparatively simple and mild conditions: inexpensive CuI as the catalyst, no separate added ligand, and C-N bond formation at room temperature. The method is compatible with a variety of functional groups, such as an olefin, a carbamate, a thiophene, and a pyridine, and it has been applied to the synthesis of an opioid receptor antagonist. A range of mechanistic observations, including reactivity and stereochemical studies, are consistent with a coupling pathway that includes photoexcitation of a copper-amidate complex, followed by electron transfer to form an alkyl radical.
