Hypervalent iodine-mediated oxidative cyclisation of p-hydroxy acetanilides to 1,2-dispirodienones.
نویسندگان
چکیده
1,2-Dispirodienones were synthesized by hypervalent iodine-mediated phenolic oxidation of p-hydroxy acetanilides. The reaction is compatible with several substituted anilides and affords a new class of 1,2-dispirodienones that are remarkably stable under thermal or acidic conditions.
منابع مشابه
Hypervalent iodine(III)-mediated oxidation of aldoximes to N-acetoxy or N-hydroxy amides.
Treatment of various aliphatic and aromatic aldoximes with the hypervalent iodine(iii) reagents (diacetoxyiodo)benzene (DIB) or Koser's reagent [hydroxy(tosyloxy)iodo]benzene (HTIB) gave, respectively, N-acetoxy or N-hydroxy amides in good yields rather than the expected nitrile oxide dimerised product oxadiazole-N-oxides reported to be formed with other oxidising and hypervalent iodine reagent...
متن کاملA novel oxidative cyclisation onto vinyl silanes.
A novel osmium-catalysed oxidative cyclisation of 1,2-diols bearing a pendant vinyl silane affords THFs that contain silicon functionality at the ring junction. When the cyclisation occurs onto a vinyl benzyldimethylsilyl group, the resulting silyl group can act as a masked hydroxyl group and undergo a Fleming-Tamao type oxidation at a later stage to form the corresponding lactol. The scope of ...
متن کاملMild hypervalent iodine mediated oxidative nitration of N-aryl sulfonamides.
An oxidative and acid-free method for the nitration of N-aryl sulfonamides has been developed using a combination of sodium nitrite as cheap and easy to handle NO2-source and the hypervalent iodine reagent PIFA as stoichiometric oxidant. Under very mild reaction conditions, the desired mononitrated aryl sulfonamides were isolated in up to 87% yield. This is the first example of an iodane-mediat...
متن کاملHypervalent iodine-mediated ring contraction reactions.
Hypervalent iodine reagents constitute a powerful tool in modern synthetic organic chemistry, promoting several important reactions. One such reaction is the ring contraction of cycloalkenes and cycloalkanones promoted by iodine(III) compounds, such as iodobenzene diacetate, iodosylbenzene, iodotoluene difluoride, and [hydroxy(tosyloxy)- iodo]benzene (Koser' s reagent). This review covers all t...
متن کاملThree component one-pot synthesis of 4H-benzo-[b]-pyran derivatives using [(diacetoxyiodo)benzene] (DIB) as a hypervalent iodine catalyst
The three components one pot synthesis of 2-amino-4H-benzo-[b] -pyran derivatives were obtained in good to excellent yields within short reaction time by condensing dimedone, aldehydes and malanonitrile or ethylcyanoacetate using a catalytic amount of (diacetoxyiodo)benzene as hypervalent iodine in aqueous ethanol under reflux conditions have been discussed. This aqua mediated Knoevenagel-cyclo...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Chemical communications
دوره 49 98 شماره
صفحات -
تاریخ انتشار 2013