K2CO3-mediated synthesis of functionalised 4-substituted-2-amino-3-cyano-4H-chromenes via Michael-cyclization reactions.
نویسندگان
چکیده
An efficient approach for the synthesis of functionalized 4-substituted-2-amino-3-cyano-4H-chromenes moderate to high yields (up to 98%) has been achieved via a tandem K2CO3 catalyzed conjugate addition-cyclization reaction of malononitrile and a range of Knoevenagel adducts previously formed from oxindole, pyrazolone, nitromethane, N,N-dimethylbarbituric acid or indanedione. This methodology differs from the previous classical methods in its simplicity and ready availability of the catalyst.
منابع مشابه
C-H Oxidation/Michael Addition/Cyclization Cascade for Enantioselective Synthesis of Functionalized 2-Amino-4H-chromenes.
A streamlined method for the enantioselective synthesis of 2-amino-4H-chromenes from readily available 2-alkyl-substituted phenols and active methylene compounds bearing a cyano group with up to 97% ee is presented. This reaction is a cascade procedure including manganese dioxide mediated C-H oxidation for the generation of o-quinone methides and bifunctional squaramide-catalyzed Michael additi...
متن کاملEfficient one-pot synthesis of 6-amino-4-aryl-5-cyano-2-methyl-4H-pyran-3-carboxylates catalyzed by nano MgO in water
Water is a versatile solvent in many ways, and in this sense performing organic reactions in this medium is now of great interest. The one-pot reaction of ethyl acetoacetate or benzyl acetoacetate, with benzaldehydes and malononitrile to provide some novel 6-amino-4-aryl-5-cyano-2-methyl-4H-pyran-3-carboxylates has been performed over nano MgO with high performance in water as a green solvent a...
متن کاملEnantioselective Organocatalyzed Synthesis of 2-Amino-3-cyano-4H-chromene Derivatives
The structural motif that results from the fusion of a benzene ring to a heterocyclic pyran ring, known as chromene, is broadly found in nature and it has been reported to be associated with a wide range of biological activity. Moreover, asymmetric organocatalysis is a discipline in expansion that is already recognized as a well-established tool for obtaining enantiomerically enriched compounds...
متن کاملSynthesis and cytotoxic activity of some 2-amino-4-aryl-3-cyano-7-(dimethylamino)-4H-chromenes
A series of 2-amino-4-aryl-3-cyano-7- (dimethylamino)-4H-chromenes was synthesized by condensation of 3- (dimethylamino) phenol, an aromatic aldehyde and malonitrile in ethanol containing piperidine. The assignments of the structure of all synthesized compounds were based on spectral data (IR, Mass and(1)H NMR). The cytotoxic activities of the synthesized compounds against six human tumor cell ...
متن کاملInorganic-organic hybrid nanomaterial (Fe3O4@SiO2-AQ): A retrievable heterogeneous catalyst for the green synthesis of 4H-chromenes
Preparation of 4-aminiquinaldine grafted on silica-coated nano-Fe3O4 particles (Fe3O4@SiO2-AQ) as a novel retrievable heterogeneous nanocatalyst is described. This novel hybrid nanomaterial was applicated for the green synthesis of substituted 2-amino-4H-chromenes via the one-pot condensation reaction of an aldehyde, malononitrile ...
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:
- Molecules
دوره 19 12 شماره
صفحات -
تاریخ انتشار 2014