51552-24-0Relevant academic research and scientific papers
Domino Aryne Annulation via a Nucleophilic-Ene Process
Xu, Hai,He, Jia,Shi, Jiarong,Tan, Liang,Qiu, Dachuan,Luo, Xiaohua,Li, Yang
supporting information, p. 3555 - 3559 (2018/03/21)
1,2-Benzdiyne equivalents possess the unique property that they can react with two arynophiles through iteratively generated 1,2- and 2,3-aryne intermediates. Upon rational modification on the second leaving group of these aryne precursors, a domino aryne annulation approach was developed through a nucleophilic-ene reaction sequence. Various benzo-fused N-heterocyclic frameworks were achievable under transition metal-free conditions with a broad substrate scope.
Diastereodivergent hydroxyfluorination of cyclic and acyclic allylic amines: Synthesis of 4-deoxy-4-fluorophytosphingosines
Cresswell, Alexander J.,Davies, Stephen G.,Lee, James A.,Morris, Melloney J.,Roberts, Paul M.,Thomson, James E.
, p. 7262 - 7281 (2012/10/30)
A diastereodivergent hydroxyfluorination protocol enabling the direct conversion of some conformationally biased allylic amines to the corresponding diastereoisomeric amino fluorohydrins has been developed. Sequential treatment of a conformationally biased allylic amine with 2 equiv of HBF 4·OEt2 followed by m-CPBA promotes epoxidation of the olefin on the face proximal to the amino group under hydrogen-bonded direction from the in situ formed ammonium ion. Regioselective and stereospecific epoxide ring-opening by transfer of fluoride from a BF 4- ion (an SN2-type process at the carbon atom distal to the ammonium moiety) then occurs in situ to give the corresponding amino fluorohydrin. Alternatively, an analogous reaction using 20 equiv of HBF4·OEt2 results in preferential epoxidation of the opposite face of the olefin, which is followed by regioselective and stereospecific epoxide ring-opening by transfer of fluoride from a BF 4- ion (an SN2-type process at the carbon atom distal to the ammonium moiety). The synthetic utility of this methodology is demonstrated via its application to a synthesis of 4-deoxy-4-fluoro-l-xylo- phytosphingosine and 4-deoxy-4-fluoro-l-lyxo-phytosphingosine, each in five steps from Garner's aldehyde.
SUBSTITUTED FLUOROETHYL UREAS AS ALPHA 2 ADRENERGIC AGENTS
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Page/Page column 43, (2008/12/04)
Therapeutic compounds, and methods, compositions, and medicaments related thereto are disclosed herein.
Highly regioselective and diastereoselective epoxidation of allylic amines with Oxone
Aggarwal, Varinder K.,Fang, Guang Yu
, p. 3448 - 3450 (2007/10/03)
Allylic amines (as their protonated ammonium salts) can be epoxidised with high syn diastereoselectivity and regioselectivity at the proximal alkene in substrates with several double bonds using Oxone. The protonated ammonium cation activates the Oxone by
Synthesis of amides with anti-inflammatory and analgesic activities
Pau,Cerri,Boatto,Palomba,Pintore,Filippelli,Falcone,Palagiano,Rossi
, p. 93 - 98 (2007/10/03)
A series of N-Aroyl-cyclohexyl- and cyclohexenylamides 3- or 4- methylsubstituted were synthesized and evaluated for their anti-inflammatory and analgesic potencies, and gastrointestinal irritation liability. One compound, N-benzoyl-4-methyl-cyclohexylamide 6a, possessed an anti- inflammatory activity comparable to that of indomethacin.
REDUCTION OF CONJUGATED CYCLOHEXENONE OXIMES WITH ALUMINIUM HYDRIDE
Zaidlewicz, Marek,Uzarewicz, Ireneusz G.
, p. 143 - 150 (2007/10/02)
The reduction of representative conjugated cyclohexenone oximes with aluminium hydride in tetrahydrofuran yields 2-cyclohexenylamines and saturated aziridines - 7-azabicycloheptane derivatives, as the main reaction products.Small quantities of cyclohexylamines and perhydroazepines are also formed.Regioselectivity of the reduction depends on oxime configuration.Higher yields of 2-cyclohexenylamines are obtained from E than Z isomers.The reaction mechanism is proposed.
