Zinc-mediated addition of diethyl bromomalonate to alkynes for the cascade reaction towards polysubstituted pyranones and tetracarbonyl derivatives.
نویسندگان
چکیده
The zinc-mediated regioselective addition reactions of diethyl bromomalonate and aromatic and aliphatic alkynes were investigated for the synthesis of vinyl malonates. When the vinyl organo-zinc intermediates were reacted with acid chlorides 2H-pyran-2-ones were obtained while the application of oxalyl chloride and an amine led to tetracarbonyl derivatives in a one-pot multi-step reaction sequence.
منابع مشابه
The reaction of diethyl bromomalonate with p-tert-butylthia-calix[4]arene: an approach to asymmetrical derivatives.
New dissymmetric and asymmetric p-tert-butylthiacalix[4]arene derivatives were prepared as a result of the reaction of p-tert-butylthiacalix[4]arene with diethyl bromomalonate in the presence of different alkali metals (Cs, K and Na) in refluxing acetone for 7 days. The structures of the prepared compounds were investigated by IR, (1)H-NMR and MALDI-TOF mass spectroscopy.
متن کاملCopper-catalyzed three-component cascade reaction of alkynes, sulfonyl azides and simple aldehydes/ketones.
A copper-catalyzed dimethylzinc-promoted three-component cascade reaction of alkynes, sulfonyl azides, and simple aldehydes or ketones is described. Polysubstituted olefins were thus constructed expeditiously in a one-pot procedure under mild conditions.
متن کاملTandem one-pot synthesis of polysubstituted NH-pyrroles involving the palladium-catalyzed intramolecular oxidative amination of the zinc bromide complex of β-enamino esters.
The Pd-catalyzed oxidative olefin amination of the zinc bromide complex intermediate, formed by the sequential reaction of nitriles with a Reformatsky reagent and 1-alkynes, affords pyrrole derivatives in good to excellent yields. This tandem protocol provides a simple, efficient, and atom- and pot-economical way to quickly build polysubstituted NH-pyrroles starting from readily available reage...
متن کاملTrimethyl Phosphite Mediated Simple Synthesis of Coumarins and Azacoumarins Through the Reaction of Phenols or Hydroxypyridines and Dimethyl Acetylenedicarboxylate (DMAD) or Diethyl Acetylenedicarboxylate (DEAD)
Protonation of the reactive intermediate produced in the reaction between trimethyl phosphite and dimethyl acetylenedicarboxylate or diethyl acetylenedicarboxylate by resorcinol, 5-methylresorcinol, 2,5-dihydroxyacetophenone, 4-chloro-2-methylphenol, 4-chloro-3,5-dimethy-lphenol, 4-hydroxypyridine, 2-hydroxypyridine, 3-hydroxypyridine, or 8-hydroxyquinoline leads to vinylphosphonium salts,...
متن کاملZinc mediated activation of terminal alkynes: stereoselective synthesis of alkynyl glycosides.
Zinc mediated alkynylation reaction was studied for the preparation of C-glycosides from unactivated alkynes. Different glycosyl donors such as glycals and anomeric acetates were tested towards an alkynyl zinc reagent obtained from alkynes using zinc dust and ethyl bromoacetate as an additive. The method provides simple, mild and stereoselective access to alkynyl glycosides both from aromatic a...
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 50 5 شماره
صفحات -
تاریخ انتشار 2014