Synthesis of α,β-unsaturated amides and iminocoumarins from N,N-disulfonyl ynamides with aldehydes via the ketenimine intermediate.
نویسندگان
چکیده
A novel synthesis of α,β-unsaturated amides from N,N-disulfonyl ynamides with aldehydes was developed. By utilization of salicylaldehydes, a variety of substituted iminocoumarins were prepared.
منابع مشابه
Enantioselective synthesis of functionalized pyrazoles by NHC-catalyzed reaction of pyrazolones with α,β-unsaturated aldehydes.
The N-heterocyclic carbene (NHC)-organocatalyzed enantioselective annulation reaction of pyrazolones with α,β-unsaturated aldehydes proceeding via the chiral α,β-unsaturated acyl azolium intermediates under oxidative conditions is presented. The reaction afforded dihydropyranone-fused pyrazoles in moderate to good yields and good er values under operationally simple and base-free conditions.
متن کاملEnantioselective Synthesis of 3,4-Dihydro-1,2-oxazepin-5(2H)-ones and 2,3-Dihydropyridin-4(1H)-ones from β-Substituted β-Hydroxyaminoaldehydes
The synthesis of 3,4-dihydro-1,2-oxazepin-5(2H)-ones and 2,3-dihydropyridin-4(1H)-ones from β-substituted β-hydroxyaminoaldehydes is reported. The β-hydroxyaminoaldehydes were prepared by enantioselective organocatalytic 1,4-addition of N-tert-butyl (tert-butyldimethylsilyl)oxycarbamate to α,β-unsaturated aldehydes (MacMillan protocol). Alkyne addition to the aldehydes followed by alcohol oxida...
متن کاملN-Heterocyclic Carbene Catalyzed Sulfenylation of α,β-Unsaturated Aldehydes.
An efficient N-heterocyclic carbene (NHC) catalyzed sulfenylation reaction of α,β-unsaturated aldehydes with N-(arylthio)phthalimide has been developed. A wide variety of α-thioenals can be obtained with good to excellent yields and excellent Z-configuration.
متن کاملChiral N-heterocyclic carbene-catalyzed generation of ester enolate equivalents from α,β-unsaturated aldehydes for enantioselective Diels–Alder reactions
The catalytic generation of chiral ester enolate equivalents from α,β-unsaturated aldehydes with chiral N-hetereocyclic carbene catalysts makes possible highly enantioselective hetero-Diels– Alder reactions. The reactions proceed under simple, mild conditions with both aliphatic and aromatic substituted enals as substrates. Previous attempts to employ these starting materials as enolate precurs...
متن کاملCopper-catalyzed aerobic oxidative amidation of terminal alkynes: efficient synthesis of ynamides.
A copper-catalyzed method for the preparation of ynamides has been identified that proceeds via aerobic oxidative coupling of terminal alkynes with various nitrogen nucleophiles, including cyclic carbamates, amides and ureas, and N-alkyl-arylsulfonamides and indoles.
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:
- Organic & biomolecular chemistry
دوره 12 23 شماره
صفحات -
تاریخ انتشار 2014