Novel Synthesis of 2-Amino-3-ethoxycarbonyl Benzopyrans with Onium Salt as Soluble Support

Task specific onium salt has been presented as soluble support in the synthesis of benzopyrans in this paper. This method allows for results by far superior to those reported other soluble supports and allows for very easy purifications of reaction products.

Efficient one-pot synthesis of 1,3-diaryl-3H-benzo[f]chromenes using ferric hydrogensulfate

An efficient and easy method for one-pot three-component synthesis of l,3-disubstituted-3H-benzo[f]chromenes by the condensation of naphtol,aromatic aldehyde derivatives and phenylacetylene in the presence of ferric hydrogensulfate[Fe（HSO4）3], has been described.The catalyst displayed high activity which afforded the corresponding 1,3-disubstituted-3H-benzo[f]chromenes in satisfying yields.Alkyl-substituted phenols were examined and the corresponding benzopyran derivatives were synthesized in moderate yields.Heterogeneous nature of the using catalyst made it reusable for further chemical reactions.

Synthesis and Crystal Structure of 2-Amino- 3-ethoxycarbonyl-4-(4-chlorophenyl)-4H, 5H-pyrano-[3,2-c]-benzopyran-5-one

The title compound 2-amino-3-ethoxycarbonyl-4-(4-chlorophenyl)-4H,5H-pyrano- [3,2-c]-benzopyran-5-one (C21H16ClNO5, Mr = 397.80) has been synthesized and characterized by X-ray crystallography. It crystallizes in triclinic, space group P1 with a = 5.756(1), b = 10.099(1), c = 17.106(3) ? a = 80.49(1), b = 83.13(1), g = 80.07(1), V = 961.8(2) ?, Dc = 1.374 g/cm3, = 0.231 mm-1, Z = 2, F(000) = 412, the final R = 0.0369 and wR = 0.0947. In the molecule the pyran ring is of boat conformation. The intermolecular hydrogen bonds of NH…O(5)(x+2, y+1, z+1) and NH…Cl (x+1, y1, z) as well as intramolecular hydrogen bond NH…O(5) are found.

Synthesis of New 2-Phenylamino-4<i>H</i>-chromene-3-carbonitrile Derivatives and Their Effects on Tumor Cell Lines and against Protein Kinases

The synthesis of 2-phenylimino-4H-chromene-3-carbonitriles 6(a-d) in good overall yields using an efficient and practical methodology in 3 steps has been implemented in this present work. The first step was a heterocyclization between 2-hydroxybenzaldehyde 1 and propanedinitrile 2 which produced 2-iminocoumarin 3 which was submitted to nitrogen/nitrogen displacement in the presence of aromatic primary amine 4. In the third step, reduction of 5 led to the desired 2-phenylimino-4H-chromene-3-carbonitriles 6. Compounds 5(a-d) and 6(a-d) were evaluated for their potential in vitro cytotoxicity against six selected tumor cell lines (Huh7-D12, Caco2, MDA-MB231, HCT 116, PC3 and NCI-H727) and tested for their protein kinase inhibition on eight selected protein kinases. Among them, compounds 5c and 6b exhibited inhibition on HsCK1e (5c: 44% and 6b: 42% at 1 μM) and 5c for cytotoxicity on PC3 cell lines (63% at 25 μM).

Two new benzopyran derivatives from Gouania leptostachya DC. var. tonkinensis Pitard.

Two new benzopyran derivatives,1-[（rel 2S,3R）-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl]ethanone（1）,and 1-[（rel 25,35）-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl]ethanone（2）,along with four known flavonoids,prodelphinidin C,prodelphinidin B3,（-）-epi-gallocatechin and（＋）-gallocatechin,were isolated from the stems of Gouania leptostachya DC.var. tonkinensis Pitard.Their structures were determined on the basis of spectroscopic methods including HR-ESI-MS,1D and 2D NMR.Prodelphinidin C exhibited significant inhibitory activity forα-glucosidase.