201424-63-7

Upstream product

• 37674-72-9 6-chloro-chroman-4-one 
• 104-88-1 4-chlorobenzaldehyde 

Downstream Products

• 934979-50-7 6-chloro-3-(4-chlorobenzyl)-2H-chromene 
• 1166789-95-2 6-chloro-3-(4-chlorobenzyl)chroman 
• 201424-66-0 6-chloro-3-(4-chlorobenzyl)chroman-4-one 
• 1166789-84-9 (Z)-6-chloro-3-(4-chlorobenzylidene)chroman 

Relevant academic research and scientific papers

Imidazolium ionic liquids as catalyst for synthesis of (E)-3- arylidene(thio)chroman-4-ones under microwave irradiation

Use of imidazolium ionic liquids [Bmim][CF3COO] and [Bmim]OH as a catalyst for synthesis of 3-arylidene(thio)chroman- 4-ones by the condensation of (thio)chroman-4-ones and aromatic aldehydes under microwave irradiation conditions. A series of 3-arylidene(thio)chroman-4-ones were obtained as the only product and considerable increase of yield was founded within short time. The products 3-arylidene(thio)chromanones were assigned the (E)-configuration based on 1H NMR spectroscopic data.

Stereocontrolled photodimerization of (E)-3-benzylidene-4-chromanones in the crystalline state: The effect of a halogen group on the chromanone moiety

A series of (E)-3-benzylidene-4-chromanone derivatives are synthesized, which are substituted with a halogen group on the chromanone moiety in order to control the molecular arrangement in the crystalline state. The stereoselective photoreactions of these compounds in the solid state are examined based on the crystal structures of the reactants and products. All the examples tested undergo photodimerization, except for (E)-3-benzylidene-6-fluorochroman-4-one. The reactants with β-structures give syn-head-to-head (syn-HH) products with high selectivity. Only (E)-6-chloro-3-(4-methylbenzylidene)-chroman-4-one adopted the α-form and gives an anti-head-to-tail (anti-HT) product. Georg Thieme Verlag KG Stuttgart · New York.

Facile condensation of aromatic aldehydes with chroman-4-ones and 1-thiochroman-4-ones catalysed by amberlyst-15 under microwave irradiation condition

Different aromatic aldehydes and cinnamaldehyde undergo crossaldol condensation with chroman-4-ones and 1-thiochroman-4-ones in the presence of amberlyst-15 under microwave irradiation in solvent free condition to afford rapidly the corresponding E-3-arylidene and E-3-cinnamylidene derivatives, respectively, in high yield. This process is simple, efficient and environmentally benign.

Synthesis and antirhinovirus activity of new 3-benzyl chromene and chroman derivatives

A series of 3-benzyl chromenes and chromans were synthesized and tested in vitro against human rhinovirus (HRV) 1B and 14, two representative serotypes for rhinovirus group B and A, respectively. All the new compounds, with the exception of 3-benzyl-2H-chromene (3a), showed a potent activity against HRV serotype 1B within micro or submicromolar range (IC50s from 0.11 to 6.62 μM). The low cytotoxicity of all the derivatives resulted in compounds with high therapeutic index (TI). On the contrary, HRV 14 infection was only weakly inhibited by the majority of these compounds. The 3-benzylidenechromans 2b and 2c showed the highest anti-HRV 1B activity (IC50 0.12 and 0.11 μM, respectively) coupled with remarkable TI (625.00 and 340.91, respectively). Mechanism of action studies on (Z)-3-(4-chlorobenzylidene)chroman (2b) suggest that the new compounds behave as capsid binders and interfere with very early stages of HRV 1B replication, similarly to related flavanoids.