76356-24-6Relevant articles and documents
UV-Light-Induced N-Acylation of Amines with α-Diketones
Xu, Zhihui,Yang, Tianbao,Tang, Niu,Ou, Yifeng,Yin, Shuang-Feng,Kambe, Nobuaki,Qiu, Renhua
supporting information, p. 5329 - 5333 (2021/07/21)
Herein, we develop a mild method for N-acylation of primary and secondary amines with α-diketones induced by ultraviolet (UV) light. Forty-six examples with various functional groups are explored at room temperature with irradiation by three 26 W UV lamps (350-380 nm). The yield reaches 97%. The gram scale experiment product yield is 76%. Moreover, this system can be applied to the synthesis of several amino acid derivatives. Mechanistic studies show that benzoin is generated in situ from benzil under UV irradiation.
Rapid Organocatalytic Formation of Carbon Monoxide: Application towards Carbonylative Cross Couplings
Zoller, Ben,Zapp, Josef,Huy, Peter H.
supporting information, p. 9632 - 9638 (2020/07/13)
Herein, the first organocatalytic method for the transformation of non-derivatized formic acid into carbon monoxide (CO) is introduced. Formylpyrrolidine (FPyr) and trichlorotriazine (TCT), which is a cost-efficient commodity chemical, enable this decarbonylation. Utilization of dimethylformamide (DMF) as solvent and catalyst even allows for a rapid CO generation at room temperature. Application towards four different carbonylative cross coupling protocols demonstrates the high synthetic utility and versatility of the new approach. Remarkably, this also comprehends a carbonylative Sonogashira reaction at room temperature employing intrinsically difficult electron-deficient aryl iodides. Commercial 13C-enriched formic acid facilitates the production of radiolabeled compounds as exemplified by the pharmaceutical Moclobemide. Finally, comparative experiments verified that the present method is highly superior to other protocols for the activation of carboxylic acids.
HEDGEHOG ACYLTRANSFERASE INHIBITORS AND USES THEREOF
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Paragraph 00272, (2018/02/24)
Hedgehog acyltransferase (Hhat), a membrane-bound O-acyl transferase (MBOAT) protein, is responsible for the palmitoylation of Shh and is crucial to proper Shh signaling. Hhat inhibitors that are capable of preventing Shh palmitoylation and mitigating Shh
ORGANIC METAL COMPLEXES AND ORGANIC LIGHT EMITTING DIODES COMPRISING THE SAME
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Paragraph 0028, (2018/02/03)
An organic metal complex is provided. The organic metal complex has the following formula (I): wherein R1 can be hydrogen, halogen, C1-12 alkyl group, C1-12 alkoxy group, amine, C2-6 alkenyl group, C2-6/su
ORGANIC METAL COMPOUND, AND ORGANIC LIGHT-EMITTING DEVICE EMPLOYING THE SAME
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Paragraph 0029, (2016/10/08)
Organic metal compounds, and organic light-emitting devices employing the same are provided. The organic metal compound has a chemical structure represented by formula (I): , wherein each R1 can be independently hydrogen, C1-12 alkyl
Modulation of Amide Bond Rotamers in 5-Acyl-6,7-dihydrothieno[3,2-c]pyridines
Lanyon-Hogg, Thomas,Ritzefeld, Markus,Masumoto, Naoko,Magee, Anthony I.,Rzepa, Henry S.,Tate, Edward W.
, p. 4370 - 4377 (2015/05/13)
2-Substituted N-acyl-piperidine is a widespread and important structural motif, found in approximately 500 currently available structures, and present in nearly 30 pharmaceutically active compounds. Restricted rotation of the acyl substituent in such molecules can give rise to two distinct chemical environments. Here we demonstrate, using NMR studies and density functional theory modeling of the lowest energy structures of 5-acyl-6,7-dihydrothieno[3,2-c]pyridine derivatives, that the amide E:Z equilibrium is affected by non-covalent interactions between the amide oxygen and adjacent aromatic protons. Structural predictions were used to design molecules that promote either the E- or Z-amide conformation, enabling preparation of compounds with a tailored conformational ratio, as proven by NMR studies. Analysis of the available X-ray data of a variety of published N-acyl-piperidine-containing compounds further indicates that these molecules are also clustered in the two observed conformations. This finding emphasizes that directed conformational isomerism has significant implications for the design of both small molecules and larger amide-containing molecular architectures. (Figure Presented).
Fused piperidines as a novel class of potent and orally available transient receptor potential melastatin type 8 (TRPM8) antagonists
Tamayo, Nuria A.,Bo, Yunxin,Gore, Vijay,Ma, Vu,Nishimura, Nobuko,Tang, Phi,Deng, Hong,Klionsky, Lana,Lehto, Sonya G.,Wang, Weiya,Youngblood, Brad,Chen, Jiyun,Correll, Tiffany L.,Bartberger, Michael D.,Gavva, Narender R.,Norman, Mark H.
experimental part, p. 1593 - 1611 (2012/04/17)
The transient receptor potential melastatin type 8 (TRPM8) is a nonselective cation channel primarily expressed in a subpopulation of sensory neurons that can be activated by a wide range of stimuli, including menthol, icilin, and cold temperatures (25 °C). Antagonism of TRPM8 is currently under investigation as a new approach for the treatment of pain. As a result of our screening efforts, we identified tetrahydrothienopyridine 4 as an inhibitor of icilin-induced calcium influx in CHO cells expressing recombinant rat TRPM8. Exploration of the structure-activity relationships of 4 led to the identification of a potent and orally bioavailable TRPM8 antagonist, tetrahydroisoquinoline 87. Compound 87 demonstrated target coverage in vivo after oral administration in a rat pharmacodynamic model measuring the prevention of icilin-induced wet-dog shakes (WDS).
Process for the preparation of 2-(2-thienyl)-ethylamine and derivatives thereof
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, (2008/06/13)
The present invention provides a process for the preparation of 2-(2-thienyl)-ethylamine and derivatives thereof having the general formula: STR1 wherein R1 and R2 are hydrogen or taken together form a phenyl ring.
The Meisenheimer Rearrangement in Heterocyclic Synthesis. III. Derivatives of the 1H-Oxazepinoindole, Thienooxazepine and Benzothienooxazepine Ring Systems
Bremner, John B.,Browne, Elaine J.,Davies, Peter E.
, p. 1335 - 1343 (2007/10/02)
The new heterocyclic derivatives 3-methyl-1-phenyl-3,4,5,10-tetrahydro-1H-oxazepino-indole (5c), 6-methyl-4-phenyl-4,6,7,8,-tetrahydrothienooxazepine (6f), and 3-methyl-1-phenyl-1,3,4,5-tetrahydrolbenzothienooxazepin
