14192-71-3Relevant articles and documents
Catalytic Amination of Phenols with Amines
Chen, Kai,Kang, Qi-Kai,Li, Yuntong,Wu, Wen-Qiang,Zhu, Hui,Shi, Hang
supporting information, p. 1144 - 1151 (2022/02/05)
Given the wide prevalence and ready availability of both phenols and amines, aniline synthesis through direct coupling between these starting materials would be extremely attractive. Herein, we describe a rhodium-catalyzed amination of phenols, which provides concise access to diverse anilines, with water as the sole byproduct. The arenophilic rhodium catalyst facilitates the inherently difficult keto–enol tautomerization of phenols by means of π-coordination, allowing for the subsequent dehydrative condensation with amines. We demonstrate the generality of this redox-neutral catalysis by carrying out reactions of a large array of phenols with various electronic properties and a wide variety of primary and secondary amines. Several examples of late-stage functionalization of structurally complex bioactive molecules, including pharmaceuticals, further illustrate the potential broad utility of the method.
Practical and regioselective amination of arenes using alkyl amines
Ruffoni, Alessandro,Juliá, Fabio,Svejstrup, Thomas D.,McMillan, Alastair J.,Douglas, James J.,Leonori, Daniele
, p. 426 - 433 (2019/05/01)
The formation of carbon–nitrogen bonds for the preparation of aromatic amines is among the top five reactions carried out globally for the production of high-value materials, ranging from from bulk chemicals to pharmaceuticals and polymers. As a result of this ubiquity and diversity, methods for their preparation impact the full spectrum of chemical syntheses in academia and industry. In general, these molecules are assembled through the stepwise introduction of a reactivity handle in place of an aromatic C–H bond (that is, a nitro group, halogen or boronic acid) and a subsequent functionalization or cross-coupling. Here we show that aromatic amines can be constructed by direct reaction of arenes and alkyl amines using photocatalysis, without the need for pre-functionalization. The process enables the easy preparation of advanced building blocks, tolerates a broad range of functionalities, and multigram scale can be achieved via a batch-to-flow protocol. The merit of this strategy as a late-stage functionalization platform has been demonstrated by the modification of several drugs, agrochemicals, peptides, chiral catalysts, polymers and organometallic complexes.
Aminobenzene compounds to prevent nerve cell degradation
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, (2008/06/13)
A compound useful for central antioxidant having inhibitory activity of degeneration and necrocytosis of cerebral cells of the formula (I): STR1 wherein A and B are independently (1) a group of the formula: STR2 wherein R1 and R2 are independently hydrogen atom, an optionally substituted hydrocarbon residue or an optionally substituted heterocyclic group, or R1 together with R2 and the nitrogen atom to which they are bound may form a cyclic amino group, provided that both R1 and R2 are not hydrogen atom at the same time, or (2) a group of the formula: STR3 wherein D is O or S, R3 is hydrogen atom, an optionally substituted hydrocarbon residue or an optionally substituted acyl group, m is 1, 2, or 3 and n is 0, 1, 2, 3 or 4; p is 1 or 2, provided that both A may be the same or different when p is 2; and R4, R5 and R6 are independently hydrogen atom, a lower alkyl or a lower alkoxy, or R5 and R6 may bond together to form --CH=CH--CH=CH--, or a salt thereof.
