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.

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 series of functionalized 4H-chromenes have been constructed by using a novel FeCl(3)-catalyzed benzylation-cyclization tandem reaction.

a series of 2-amino-4-aryl-3-cyano-7-(dimethylamino)-4 h -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 l...

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.

A linear quantitative structure-activity relationship (QSAR) model is presented for modeling and predicting induction of apoptosis by 4-aryl-4H-chromenes. The model was produced by using the multiple linear regression (MLR) technique on a database that consists of 43 recently discovered 4-aryl-4H-chromenes. Among the 61 different physicochemical, topological, and structural descriptors that wer...

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.

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 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.