First iron-catalyzed guanylation of amines: a simple and highly efficient protocol to guanidines
نویسندگان
چکیده
The first iron-catalyzed guanylation of amines is reported. Commercially available Fe(OAc)2 acts as an excellent catalyst for the addition of amines to carbodiimides. The reaction is broadly applicable to a variety of primary, secondary, and heterocyclic amines, and tolerates a wide range of functionalities allowing the easy preparation of a large family of guanidines. The low price and low toxicity of the commercially available iron catalyst make this methodology highly attractive. 2012 Elsevier Ltd. All rights reserved. R1R2NH + RN=C=NR Catalyst R2 = H for primary amines N NHR
منابع مشابه
Facile and mild synthesis of 1-substituted-1H-1,2,3,4-tetrazoles catalyzed by methanesulfonic acid under solvent-free conditions
Methanesulfonic acid (MSA) was found to be an efficient catalyst for the synthesis of 1-substituted-1H-1,2,3,4-tetrazoles. A series of 1-substituted tetrazole compounds were synthesized from the reaction of various primary amines, sodium azide and triethyl orthoformate in the presence of catalytic amounts of MSA at room temperature. In this protocol, some of the tetrazole derivatives were synth...
متن کاملFacile and mild synthesis of 1-substituted-1H-1,2,3,4-tetrazoles catalyzed by methanesulfonic acid under solvent-free conditions
Methanesulfonic acid (MSA) was found to be an efficient catalyst for the synthesis of 1-substituted-1H-1,2,3,4-tetrazoles. A series of 1-substituted tetrazole compounds were synthesized from the reaction of various primary amines, sodium azide and triethyl orthoformate in the presence of catalytic amounts of MSA at room temperature. In this protocol, some of the tetrazole derivatives were synth...
متن کاملHighly efficient one-pot four-component synthesis of polyhydroquinoline derivatives catalyzed by stannous chloride under solvent-free conditions
A rapid and efficient one-pot, four-component protocol towards the synthesis of polyhydroquinoline derivatives has been developed. The condensation of aldehyde, dimedone, ethyl acetoacetate and ammonium acetate in presence of stannous chloride was carried out under solvent free condition to synthesize a variety of polyhydroquinoline derivatives in good to excellent yields. Stannous chloride was...
متن کاملA Simple and Effective Protocol for One-Pot Diazotization-Iodination of Aromatic Amines by Acidic Ionic Liquid [H-NMP]HSO4 at Room Temperature
A simple and efficient one-pot method for the preparation of aromatic iodides has been developed by sequential diazotization–iodination of aromatic amines employing sodium nitrite and sodium iodide in the presence of acidic ionic liquid N-methyl-2-pyrrolidonum hydrosulfate ([H-NMP]HSO4). The diazonium salts that are formed by this ionic liquid are stable at room temperature and r...
متن کاملHighly efficient one-pot four-component synthesis of polyhydroquinoline derivatives catalyzed by stannous chloride under solvent-free conditions
A rapid and efficient one-pot, four-component protocol towards the synthesis of polyhydroquinoline derivatives has been developed. The condensation of aldehyde, dimedone, ethyl acetoacetate and ammonium acetate in presence of stannous chloride was carried out under solvent free condition to synthesize a variety of polyhydroquinoline derivatives in good to excellent yields. Stannous chloride was...
متن کامل