- A Friedlaender approach to novel 1,10-phenanthrolines and their use as ligands for Ru(II) and Cu(I)
-
A six step synthesis of 8-amino-7-quinolinecarbaldehyde from 8-hydroxyquinoline has been developed. This aminoaldehyde undergoes Friedlaender condensation with ketones to form 2-substituted 1,10-phenanthrolines and 1,2-diketones to form 2,2′-bi-(1.10-phenanthroline)s. A tetramethylene derivative of the latter class of compounds forms a helical dinuclear complex with Cu(I).
- Hung, Chi-Ying,Wang, Tie-Lin,Shi, Zhiqiang,Thummel, Randolph P.
-
-
Read Online
- Merging Annulation with Ring Deconstruction: Synthesis of (E)-3-(2-Acyl-1 H-benzo[ d]imidazol-4-yl)acrylaldehyde Derivatives via I2/FeCl3-Promoted Dual C(sp3)-H Amination/C-N Bond Cleavage
-
An unprecedented I2/FeCl3-promoted cascade reaction of aryl methyl ketones with 8-aminoquinolines for the convenient synthesis of (E)-3-(2-acyl-1H-benzo[d]imidazol-4-yl)acrylaldehydes was developed by merging annulation with ring deconstruction. This novel strategy unlocked the new reactivity of 8-aminoquinolines and provided an attractive platform for the ring opening of unactivated N-heteroaromatic compounds. Preliminary mechanistic investigation suggested that dual C(sp3)-H amination/C-N bond cleavage were key reaction steps. Furthermore, late-stage modification of the obtained products successfully delivered pyrazole and isoxazole derivatives, increasing the practicability and application potential of this methodology in organic synthesis.
- Xu, Cheng,Yin, Guodong,Jia, Feng-Cheng,Wu, Yan-Dong,Wu, An-Xin
-
p. 2559 - 2564
(2021/04/13)
-
- Design and synthesis of chiral 1,10-phenanthroline ligand, and application in palladium catalyzed asymmetric 1,4-addition reactions
-
Pd-catalyzed asymmetric 1,4-addition of phenylboronic acid to α,β-unsaturated carbonyl compounds was developed using chiral 1,10-phenanthroline derivative as ligand. Good yields (up to 97%), and high enantioselectivities (up to 97% ee) were achieved.
- Tamura, Masafumi,Ogata, Hayato,Ishida, Yuu,Takahashi, Yasunori
-
p. 3808 - 3813
(2017/09/15)
-
- Novel Sulfonaminoquinoline Hepcidin Antagonists
-
The present invention relates to novel hepcidin antagonists, pharmaceutical compositions comprising them and the use thereof as medicaments for the use in the treatment of iron metabolism disorders, such as, in particular, iron deficiency diseases and anemias, in particular anemias in connection with chronic inflammatory diseases.
- -
-
-
- Introduction of benzo[h]quinoline and 1,10-phenanthroline subunits by friedl?nder methodology
-
An improved preparation of 8-amino-7-quinolinecarbaldehyde has been developed. The methyl group of 7-methyl-8-nitroquinoline may be oxidized to an aldehyde by treatment first with dimethylformamide dimethyl acetal followed by sodium periodate. Reduction with iron provides the amino aldehyde. An analogous sequence affords 1-amino-2-naphthalenecarbaldehyde. Friedl?nder condensation of the quinoline derivative with a series of acetylaromatics provides the corresponding 2-aryl-1,10-phenanthrolines. Condensation of either amino aldehyde with 1,3-diacetylbenzene or 2,6-diacetylpyridine provides the expected Friedl?nder product. Similar chemistry is described for reactions of the amino aldehydes with 1,4-diacetylbenzene, 4,4′-diacetylbiphenyl, 1,5-diacetylanthracene, 1,2,3,4,5,6,7,8-octahydroacridine-1,8-dione, and tetracyclo-[6.3.0.0.4,1105,9]undecane-2,7-dione (TCU-2,7-dione).
- Riesgo, Elvira C.,Jin, Xiaoqing,Thummel, Randolph P.
-
p. 3017 - 3022
(2007/10/03)
-