2-Amino-3-cyano-4H-chromenes show great potential as novel anticancer agents. Here we report a quinine-catalyzed highly enantioselective formal 4 + 2 cycloaddition of ortho-quinone methides and malononitrile, providing a unique approach to 4-arylvinyl, 4-aryl and 4-vinyl 2-amino-3-cyano-4H-chromenes with excellent yields and enantioselectivities. Moreover, this reaction can be performed in up t...

A three-component cascade reaction of salicylaldehyde, malononitrile/cyanoacetate and nitromethane catalysed by chiral tertiary amino-thioureas was developed, which leads to the production of highly functionalized 2-amino-4H-chromenes in good yields with good to excellent enantioselectivities.

Silica-bonded n-propyltriethylene-tetramine (SBNPTT) was found as an efficient solid base for the synthesis of 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromenes. Chromene derivatives were obtained via the three-component condensation reaction of aromatic aldehydes, malononitrile, and dimedone at 80 oC under solvent-free conditions. The heterogeneous solid base showed much the same efficiency when u...

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...

silica-bonded n-propyltriethylene-tetramine (sbnptt) was found as an efficient solid base for the synthesis of 2-amino-5-oxo-5,6,7,8-tetrahydro-4h-chromenes. chromene derivatives were obtained via the three-component condensation reaction of aromatic aldehydes, malononitrile, and dimedone at 80 oc under solvent-free conditions. the heterogeneous solid base showed much the same efficiency when u...

A one-pot three-component condensation of an aldehyde, malononitrile, and resorcinol has been achieved by ultrasound method. The reaction has been catalyzed by glycine in aqueous medium. This protocol afforded corresponding 2-amino-4H-chromenes in shorter reaction times, high yields and simple work-up procedures with the green aspects by avoiding toxic reagents.

Silica tungstic acid (STA) has been found to be an efficient and reusable solid acid catalyst for the synthesis of 2-amino-4H-chromenes via the three-component reaction of aromatic aldehydes, malononitrile, and β-naphthol. STA as a novel solid acid was characterized by X-ray fluorescence, X-ray diffraction, and Fourier transform infrared spectroscopy.

ABSTRACT A simple and efficient approach has been developed to synthesise novel functionalised 5H-chromeno[2,3-d] pyrimidines derivatives (4a-h). This entails treating 2-amino-3-cyano-4H-chromenes (3a-h) with formamidine acetate under microwave irradiations solvent-free conditions. All structures of new compounds obtained in this study were characterised by IR, MS, 1H 13C NMR analysis. Addition...

Silica-bonded n-propyltriethylene-tetramine (SBNPTT) was found as an efficient solid base for the synthesis of 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromenes. Chromene derivatives were obtained via the three-component condensation reaction of aromatic aldehydes, malononitrile, and dimedone at 80 oC under solvent-free conditions. The heterogeneous solid base showed much the same efficiency when u...

A catalytic asymmetric oxidative iminium-allenamine cascade allows the use of propargyl alcohols as stable substrates and yields valuable chiral bicyclic 4H-chromenes. A subsequent Michael addition-condensation domino reaction provides complex tricyclic 4H-chromenes in a highly enantioselective fashion.