One‐Pot Synthesis of 3‐Cyano‐2‐pyridones

Abstract

A versatile synthesis of 3‐cyano‐2‐pyridones via a one‐pot, four‐component condensation of ethyl cyanoacetate, ketones, aldehydes, and ammonium acetate under very mild conditions has been developed. This method provides rapid access to this type of valuable heterocyclic compounds from readily available materials in a single operation.

An Efficient One‐Pot Synthesis of Highly Substituted Pyridone Derivatives and Their Antimicrobial and Antifungal Activity

“…Literature survey reveals that only a few methods have been reported for one‐pot synthesis of pyridones by condensation of three components, an aldehyde, a β ‐ketoester, and cyanoacetate or cyanoacetamide under acidic or basic conditions such as HNO 3 , H 2 SO 4 , Piperidine, NH 4 OAc, ZnO, SOCl 2 , and so on . However, these methods suffer from very low yields and harsh reaction conditions.…”

Synthesis of 1,6-Dihydropyridine-3-carbonitrile Derivatives via Lewis Acid-Catalyzed Annulation of Propargylic Alcohols with (E)-3-Amino-3-phenylacrylonitriles

“…For example, a milrinone analogue, isolated from reserpine-treated guinea pigs, was identified as the most effective and selective inotropic agent for the treatment of chronic heart failure, with a weak influence on frequency rate . Olprinone, belonging to the family of phosphodiesterase III inhibitors, exhibits therapeutic activity for heart failure . A-769662, as an activator of AMP-activated protein kinase, could affect the metabolic switch from an anabolic to a catabolic state .…”

Synthesis of 4-aryl-6-phenyl-3-cyano-2-pyridones Using l-Proline as an Organocatalyst

“…2-Pyridone derivatives are also used in the manufacturing of paints, pigments, additives for fuels and lubricants, acid-base indicators, stabilizers for polymers and coatings [10]. The 3-cyano-2-pyridones can be resulted by different methods and various starting materials including pyrrolidine [11], microwave [12] and the other references in reported literatures [13,14]. 4,6-Diaryl-2-oxo-1,2-dihydropyridine-3-carbonitriles can be prepared by cyclization of ethyl cyanoacetate and ketones by ammonium acetate [15], reaction between 1,3-diaryl-2-propen-1-one and cyanoacetamide using CH 3 ONa [16], piperidine [17] or DMSO-tert-BuOK [18], the reaction of β-aminoenones with substituted acetonitriles [19], the reaction of malononitrile with acetylenic ketones [20], Polystyrene/1% divinylbenzene sodium benzenesulfinate, an alkyl or aryl bromide, alkyl or aryl epoxide, tert-butoxide/DMSO, malonamide or methyl malonate monoamide, and 2-cyanoacetamide [21], and three-component cyclocondensation from aromatic aldehydes, aromatic ketones, and 2-cyanoacetamide under solvent-free [22].…”