Trimethylsilyl chloride promoted synthesis of α-branched amines by nucleophilic addition of organozinc halides to nitrones.

نویسندگان

  • Ying Fu
  • Yanhua Liu
  • Yaojuan Chen
  • Helmut M Hügel
  • Minzhu Wang
  • Danfeng Huang
  • Yulai Hu
چکیده

A general procedure for the nucleophilic addition of organozinc halides with nitrones in the presence of trimethylsilyl chloride has been developed. Trimethylsilyl chloride was found to be both an indispensable reaction promoter and a ready hydroxylamine protective agent in these reactions. The produced O-(trimethylsilyl)hydroxylamines can be easily reduced into corresponding amines just by a zinc-copper couple in saturated aqueous NH(4)Cl solution.

برای دانلود رایگان متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Ultrasound-promoted Catalyst-free Synthesis of α-Aminonitriles in 1-Butyl-3-methylimidazolium Bromide ([Bmim]Br) as a Reusable Neutral Ionic Liquid

A catalyst-free one-pot three component methodology for the synthesis of α-aminonitriles under ultrasonic irradiation at room temperature using [Bmim]Br as a neutral reaction medium is described. A broad range of substrates including the aromatic, heteroaromatic and aliphatic aldehydes were condensed with amines (aliphatic and aromatic) and trimethylsilyl cyanide (TMSCN). Using this method, all...

متن کامل

Coupling of Amines, Dialkyl acetylenedicarboxylaes and Formaldehyde Promoted by Copper (II) Chloride: An Efficient Synthesis of Polysubstituted Dihydro-2-oxopyrrols

An environmental friendly synthetic route for copper (II) chloride dihydrate catalyzed one-pot multicomponentsynthesis of biologically active high substituted dihydro-2-oxypyrroles has developed. The non-toxic, low-cost catalyst and eco-friendly and good to high yields are the notable benefits for the efficient synthesis of these products.

متن کامل

CuI catalyzed sulfonylation of organozinc reagents with sulfonyl halides.

In this study, a facile CuI catalyzed synthesis of sulfones involving a nucleophilic addition of functionalized organozinc reagents to organic sulfonyl chlorides is realized. This reaction proceeds efficiently at room temperature, giving rise to various functional group substituted sulfones, generally in moderate to high yields. The method provides a novel, simple, and promising strategy for fu...

متن کامل

A truly green synthesis of α-aminonitriles via Strecker reaction

BACKGROUND The classical Strecker reaction is one of the simplest and most economical methods for the synthesis of racemic α-aminonitriles (precursor of α-amino acids) and pharmacologically useful compounds. RESULTS Indium powder in water is shown to act as a very efficient catalyst for one-pot, three-component synthesis of α-aminonitriles from diverse amines, aldehydes and TMSCN. This genera...

متن کامل

Docking Studies, Synthesis, and In-vitro Evaluation of Novel Oximes Based on Nitrones as Reactivators of Inhibited Acetylcholinesterase

Acetylcholinesterase has important role in synaptic cleft. It breaks down the acetylcholineatcholinergic synapsesand terminates the cholinergic effects. Some chemical agents likeorganophosphorus compounds (OPCs) including nerve agents and pesticides react withacetylcholinesteraseirreversibly. They inhibit normal biological enzyme action and resultin accumulation of acetylcholineand show toxic e...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

عنوان ژورنال:
  • Organic & biomolecular chemistry

دوره 10 38  شماره 

صفحات  -

تاریخ انتشار 2012