4675-18-7Relevant academic research and scientific papers
Fast-Synthesis of α-Phosphonyloxy Ketones as Drug Scaffolds in a Capillary Microreactor
Ramanjaneyulu, Bandaru T.,Vidyacharan, Shinde,Yim, Se Jun,Kim, Dong-Pyo
, p. 7730 - 7734 (2019/12/24)
A simple, room temperature approach for the fast single-step synthesis of α-phosphonyloxy ketone, a drug scaffold, has been developed which involves highly reactive species i.e., 1,2-dicarbonyls that readily react with trialkyl phosphites and formic acids in batch as well as in continuous-flow with the flow rate of 3 ml/min (tR = ～4 s). The present approach reduced the synthesis time from hours to minutes in batch, which was further lowered to a few seconds precisely controlled by single capillary microfluidics. A wide range of 1,2-dicarbonyl derivatives were smoothly transformed to their corresponding α-phosphonyloxy ketones in moderate to good yields (50–82 %) under optimized flow-reaction conditions. Further, the α-phosphonyloxy ketones produced can be utilized in batch process to form benzoin, oxazole core, and α,α′-diarylated carbonyl compounds in 82 %, 50 %, and 54 % yields, respectively, which are alternative key precursors/scaffolds of natural products and active pharmaceutical ingredients (APIs).
Microwave-assisted conversion of carbonyl compounds into formylated secondary amines: New contribution to the Leuckart reaction mechanism in N-methylformamide
Barba, Fructuoso,Recio, Javier,Batanero, Belen
, p. 1835 - 1838 (2013/04/24)
The reductive amination of several carbonyl compounds (Leuckart reaction) has been performed using N-methylformamide and microwave technology. Under these conditions, a new mechanism is proposed via the initial formation of an imine, followed by reduction
A method for the reductive scission of heterocyclic thioethers
Graham, Thomas H.,Liu, Wensheng,Shen, Dong-Ming
supporting information; experimental part, p. 6232 - 6235 (2012/01/03)
A mild, chemoselective, and generally high-yielding method for the reductive scission of heterocyclic thioethers is described. Suitable heterocycles have a thioether substituent at the 2-position relative to a ring heteroatom. The convenient and straightforward method is demonstrated with reactants which are not compatible with the standard Raney nickel conditions such as sulfides, sulfones, and thiophenes. In addition, benzyl esters, benzyl amides, and benzyl carbamates are tolerated by the reductive reaction conditions.
HETEROARYL COMPOUNDS AND METHODS OF USE THEREOF
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Page/Page column 111, (2011/12/14)
Provided herein are heteroaryl compounds, methods of their synthesis, pharmaceutical compositions comprising the compounds, and methods of their use. In one embodiment, the compounds provided herein are useful for the treatment, prevention, and/or management of various disorders, such as CNS disorders and metabolic disorders, including, but not limited to, e.g., neurological disorders, psychosis, schizophrenia, obesity, and diabetes
Synthesis of azirines containing aldehyde functionality and their utilization as synthetic tools for five membered oxazoles and isoxazoles
Brahma, Sulagna,Ray, Jayanta K.
, p. 311 - 317 (2008/09/20)
(Chemical Equation Presented) A simple and useful procedure for the synthesis of azirines containing aldehyde functionality from open chain bromo/chloro-aldehydes at room temperature is reported. The scope of the ring expansion reaction of a number of 3-s
Ceric ammonium nitrate promoted oxidation of oxazoles
Evans, David A.,Nagorny, Pavel,Xu, Risheng
, p. 5669 - 5671 (2007/10/03)
The ceric ammonium nitrate promoted oxidations of 4,5-diphenyloxazoles and oxazoles with various substitution patterns have been investigated. This transformation results in the formation of the corresponding imide in good yield and tolerates a wide variety of functional groups and substituents on the oxazole moiety.
Inhibitors of fatty acid amide hydrolase
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Page/Page column 11, (2008/06/13)
Improved competitive inhibitors of FAAH employ an α-keto heterocyclic pharmacophore and a binding subunit having a ?-unsaturation. The α-keto heterocyclic pharmacophore and a binding subunit are attached to one another, preferably by a hydrocarbon chain. The improvement lies in the use of a heterocyclic pharmacophore selected from oxazoles, oxadiazoles, thiazoles, and thiadiazoles that have alkyl or aryl substituents at their 4 and/or 5 positions. The improved competitive inhibitors of FAAH display enhanced activity over conventional competitive inhibitors of FAAH.
Discovery of a potent, selective, and efficacious class of reversible α-ketoheterocycle inhibitors of fatty acid amide hydrolase effective as analgesics
Boger, Dale L.,Miyauchi, Hiroshi,Du, Wu,Hardouin, Christophe,Fecik, Robert A.,Cheng, Heng,Hwang, Inkyu,Hedrick, Michael P.,Leung, Donmienne,Acevedo, Orlando,Guimar?es, Cristiano R. W.,Jorgensen, William L.,Cravatt, Benjamin F.
, p. 1849 - 1856 (2007/10/03)
Fatty acid amide hydrolase (FAAH) degrades neuromodulating fatty acid amides including anandamide (endogenous cannabinoid agonist) and oleamide (sleep-inducing lipid) at their sites of action and is intimately involved in their regulation. Herein we report the discovery of a potent, selective, and efficacious class of reversible FAAH inhibitors that produce analgesia in animal models validating a new therapeutic target for pain intervention. Key to the useful inhibitor discovery was the routine implementation of a proteomics-wide selectivity screen against the serine hydrolase superfamily ensuring selectivity for FAAH coupled with systematic in vivo examinations of candidate inhibitors.
N-H Insertion reactions of rhodium carbenoids. Part 5: A convenient route to 1,3-azoles
Davies, James R.,Kane, Peter D.,Moody, Christopher J.
, p. 3967 - 3977 (2007/10/03)
Dirhodium(II) carboxylate catalysed reaction of diazocarbonyl compounds 2 in the presence of primary amides 1 results in the formation of α-acylaminoketones 3 (12 examples) by N-H insertion reaction of the intermediate rhodium carbene. The 1,4-dicarbonyl
Convenient syntheses of 2-alkyl(Aryl)-4,5-diphenyloxazoles and 2-alkyl(Aryl)-4-phepyloxazoles
Pei, Weiwei,Li, Shaohui,Nie, Xiaoping,Li, Yiwei,Pei, Jian,Chen, Bingzi,Wu, Jie,Ye, Xiulin
, p. 1298 - 1304 (2007/10/03)
The synthetic methods to prepare 2-alkyl(aryl)-4,5-diphenyloxazoles and 2-alkyl(aryl)-4-phenyloxazoles were improved on the basis of a mechanistic study of oxazole formation from α-hydroxy ketones (carboxylic esters of benzoin and phenacyl alcohols). By these methods, seven trisubstituted oxazoles and twelve disubstituted oxazoles of the title compounds were prepared.
