An a-aminomethyl carbanion equivalent via a novel Barbier reaction: (1H-naphtho[1,8-de]-1,2,3-triazin-2-yl)methyl anion
نویسنده
چکیده
A novel sonication-promoted Barbier reaction putatively generated the titled species from the corresponding naphthotriazinylmethyl chloride and magnesium in THF: its formal addition to a variety of carbonyl compounds in situ occurred in excellent yields. Subsequent catalytic hydrogenolysis of the triazine moiety demasked the amine, thus de®ning a route to various phenylethylamines (including the alkaloid `mescaline'), or ethanolamines (in two cases), in excellent overall yields. # 2000 Elsevier Science Ltd. All rights reserved.
منابع مشابه
The Length Dependent Activity of Oximes on Reactivation of Tabun Inhibited Acetylcholinesterase; A Theoretical Study
In this work, the effect of ligand's length on interaction energy of six oximes, A [2-(hydroxyimino)-N-((1-(2-(2-((hydroxyimino)methyl)-1H-imidazol-1-yl)ethyl)-1H-1,2,3-triazol-4-yl)methyl)acetamide], B [2-(hydroxyimino)-N-((1-(3-(2-((hydroxyimino)methyl)-1H-imidazol-1-yl)propyl)-1H-1,2,3-triazol-4-yl)methyl)acetamide], C [2-(hydroxyimino)-N-((1-(4-(2-((hydroxyimino)methyl)-1H-imidazol-1-yl)but...
متن کاملSynthesis, characterization and polymerization of a novel acrylate monomer containing both 4H-pyran-4-one and 1,2,3-triazole moiety and evaluation of their antibacterial activity
A novel acrylate monomer containing 4H-pyran-4-one and 1,2,3-triazole ring, {1-[4-(4-oxo-6-phenyl-4H-pyran-2-yl)benzyl]-1,2,3-triazol-4-yl}methyl acrylate was synthesized by the reaction of 2-{4-[(4-(hydroxymethyl)-1,2,3-triazol-1-yl)methyl]phenyl}-6-phenyl-4H-pyran-4-one with acryloyl chloride in the presence of triethylamine. The structure of the acrylate monomer was established on the basis ...
متن کاملSynthesis of 2-(aminomethyl)aziridines and their microwave-assisted ring opening to 1,2,3-triaminopropanes as novel antimalarial pharmacophores.
A variety of 2-(aminomethyl)aziridines was prepared and converted into the corresponding 1,2,3-triaminopropanes through a novel, microwave-assisted and regioselective ring opening by diethylamine in acetonitrile. Antiplasmodial assays revealed antimalarial activity for 2-[(1,2,4-triazol-1-yl)methyl]aziridines and 2-(N,N-diethylaminomethyl)aziridines, as well as for the corresponding 1-(diethyla...
متن کاملSynthesis and cytotoxicity evaluation of some novel thiazoles, thiadiazoles, and pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidin-5(1H)-ones incorporating triazole moiety.
Reactions of hydrazonoyl halides and each of methyl 2-(1-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)ethylidene)hydrazine-1-carbodithioate and 2-(1-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)ethylidene)hydrazine-1-carbothioamide afforded 2-(1-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)ethylidene)hydrazono)-3-phenyl-5-substituted-2,3-dihydro-1,3,4-thiadiazoles and 5-(4-substituted)diazenyl)-2-(2-(1-(5-...
متن کاملGreen and diastereoselective synthesis of trans-3-(5-methylisoxazol-3-yl)-3,4-dihydro-2H-naphtho[2,3-e][1,3]oxazines
Reaction between aromatic aldehydes and 3–methyl-1-phenyl-2-pyrazoline-5-one catalyzed by nano-SiO2/HClO4 in water under reflux provided a simple and efficient route for the synthesis of 4-((5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)(aryl)methyl)-3-methyl-1-phenyl-1H-pyrazol-5-ol derivatives in high yields.
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
دوره شماره
صفحات -
تاریخ انتشار 2000