One-pot synthesis of GABA amides via the nucleophilic addition of amines to 3,3-disubstituted cyclopropenes.
نویسندگان
چکیده
A one-pot synthesis of various GABA amides has been demostrated, employing the nucleophilic addition of primary and secondary amines across the double bond of cyclopropene-3-carboxamides, followed by ring-opening of the resulting donor-acceptor cyclopropanes and subsequent in situ reduction of enamine (imine) intermediates.
منابع مشابه
An Efficient One Pot Procedure for Preparation of Symmetrical N,N'-Disubstituted Urea from Aromatic and Aliphatic Amines and Urea under Microwave Irradiation
A phosgene-free synthesis of symmetrical N,N'-disubstituted urea by the reaction of aromatic and aliphatic primary amines and urea promoted by microwave irradiation in the presence of a suitable energy-transfer solvent such as N-N-dimethylacetamide is described.
متن کاملSynthesis of 3,3-disubstituted oxindoles by one-pot integrated Brønsted base-catalyzed trichloroacetimidation of 3-hydroxyoxindoles and Brønsted acid-catalyzed nucleophilic substitution reaction.
Treatment of 3-hydroxyoxindoles with trichloroacetonitrile (1.3 equiv.) and a catalytic amount of DBU (0.1 equiv.) followed by addition of nucleophiles (1.5 equiv.) and diphenylphosphoric acid (0.2 equiv.) afforded the 3,3-disubstituted oxindoles in good to excellent yields. DFT computations supported the notion that the reaction went through the 1-alkyl-2-oxo-2H-indol-1-ium intermediate.
متن کاملTin powder-promoted one-pot synthesis of 3-spiro-fused or 3,3'-disubstituted 2-oxindoles.
A convenient and efficient method for the constructions of 3-spirooxindole derivatives or 3,3'-disubstituted oxindoles has been developed from one-pot reactions of isatins, hydrazides or aromatic amines, 2-(bromomethyl)acrylic ester and tin powder in the presence of a catalytic amount of Brønsted or Lewis acid. The method avoids the use of toxic stannanes and allows easy operation. It is also p...
متن کاملOne-pot multicomponent click synthesis of some novel 1,4-disubstituted-1H-1,2,3-triazoles from alkenes
A facile and one-pot multicomponent synthesis of novel 1,4-disubstituted-1H-1,2,3-triazoles from alkenes at room temperature is reported. At the first step, in the presence of I2/NaN3 reagents, various alkenes were converted to the corresponding azido iodides and in the next step, the reaction of these compounds with phenylacetylene in the presence of catalytic amount of sodium ascorbate/ CuSO4...
متن کاملOne-pot synthesis of diverse N,N'-disubstituted guanidines from N-chlorophthalimide, isocyanides and amines via N-phthaloyl-guanidines.
A sequential one-pot approach towards N,N'-disubstituted guanidines from N-chlorophthalimide, isocyanides and amines is reported. This strategy provides straightforward and efficient access to diverse guanidines in yields up to 81% through previously unprecedented N-phthaloylguanidines. This protocol also features wide substrate scope and mild conditions.
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 13 34 شماره
صفحات -
تاریخ انتشار 2015