Improved Cope-type hydroamination reactivity of hydrazine derivatives.
نویسندگان
چکیده
A systematic investigation on the metal-free, Cope-type hydroamination reactivity of hydrazides and analogues is reported. Optimization of the hydrazide structure resulted in more facile intramolecular reactivity and enabled intermolecular reactions of alkenes, thus providing a direct approach to polysubstituted hydrazides.
منابع مشابه
A theoretical study on the mechanisms of the reactions between 1,3-dialkynes and ammonia derivatives for the formation of five-membered N-heterocycles.
The reactions between 1,3-dialkynes and ammonia derivatives (such as hydrazine and hydroxylamine) for the formation of five-membered N-heterocycles (i.e. 3,5-disubstituted pyrazole and 3,5-disubstituted isoxazole) have been investigated using the density functional theory (DFT) method. The calculated results indicate that the favorable mechanism of this kind of reaction generally contains four ...
متن کاملSynthesis of 3,5-disubstituted pyrazoles via Cope-type hydroamination of 1,3-dialkynes.
An efficient method for the synthesis of 3,5-disubstituted pyrazoles is described. The reactions of 1,3-dialkynes with hydrazine proceeded smoothly in dimethyl sulfoxide under mild reaction conditions to produce 3,5-disubstituted pyrazoles in satisfactory to excellent yields. A one-pot procedure of the transformation has been developed.
متن کاملHydroamination of Terminal Alkynes by Amines Catalyzed by Copper Heteropoly Salts: A Simple Approach Towards Imine Synthesis
The hydroamination reaction offers a very attractive route for the synthesis of alkylated amines and their derivatives with no byproduct formation. Heterogeneous intermolecular hydroamination reactions of alkynes with aromatic amines using different inexpensive copper salts of hetropolyacid catalysts were investigated. Among heteropoly salts, copper salts of silicotungstic acid showed highest a...
متن کاملSynthesis, characterization, and antimicrobial evaluation of novel 5-benzoyl-N-substituted amino- and 5-benzoyl-N-sulfonylamino-4-alkylsulfanyl-2-pyridones
The present research describes the synthesis of novel 5-benzoyl-N-substituted-amino- and 5-benzoyl-N-sulfonylamino-4-alkylsulfanyl-2-pyridones 5a-c and 6a-c via the reaction of 2-benzoyl-3,3-bis(alkylthio)acrylonitriles 2a-c with N-cyanoacetohydrazide 3 and cyanoaceto-N-phenylsulfonylhydrazide 4, respectively. Also, the reactivity of the compounds 5a-c toward hydrazine hydrate to give product 1...
متن کاملSynthesis and antibacterial evaluation of novel heterocyclic compounds containing a sulfonamido moiety.
Aiming for the synthesis of new heterocyclic compounds containing a sulfonamido moiety suitable for use as antibacterial agents, the precursor ethyl {[4-N-(4,6-dimethylpyrimidin-2-yl)sulfamoyl]phenylazo}cyanoacetate was reacted with a variety of active methylene compounds producing pyran, pyridine and pyridazine derivatives. Also, the reactivity of the precursor hydrazone towards hydrazine deri...
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 47 1 شماره
صفحات -
تاریخ انتشار 2011