Rongbi Han

Indium-mediated one-pot reductive conversion of nitroarenes to N-arylacetamides

N-Arylacetamides were prepared in excellent yields from nitroarenes in the presence of acetic anhydride, acetic acid and indium by a one-pot procedure.

Indium mediated reductive heterocyclization of 2-nitroacylbenzenes or 2-nitroiminobenzenes toward 2,1-benzisoxazoles in aqueous media

2-Nitro-substituted acylbenzenes or iminobenzenes such as 2-nitrobenzaldehydes, 2′-nitroacetophenone, and N-(2-nitrobenzylidene)anilines were cyclized toward 2,1-benzisoxazoles in the presence of 2-bromo-2-nitropropane and indium in an MeOH/H2O solution in excellent yields.

Asymmetric Allylation of Aldimines with Indium and (+)‐Cinchonine

Abstract By applying indium and allyl bromide, aldimines were converted into homoallyl amines with excellent yields. The addition of (+)‐cinchonine to the reaction mixture yielded enantioselective allylation with 22–44% ee.

INDIUM MEDIATED REDUCTIVE ACYLATIONS OF NITROARENES TOWARDS N,O-DIACYLATED N-ARYLHYDROXYLAMINES*

By applying indium, Ac2O, MeOH, and catalytic amount of InCl3 in CHCl3 solution, nitroarenes were transformed into N,O-diacylated N-arylhydroxylamines in moderate to excellent yields. *Dedicated to Professor Jack W. Timberlake on the occasion of his 60th Birthday.

SmI2 MEDIATED ALLYLATION OF ALDIMINES WITH ALLYL BROMIDE

In a mild reaction with SmI2, aldimines have been converted into homoallyl amines in good yields.

Synthesis of Novel 8-alkylamino-5, 6-dihydro-4H-benzo[f] [1,2,4]triazolo [4,3-a]azepines as Anticonvulsant Agents.

A series of new 8-alkylamino-5, 6-dihydro-4H-benzo[f][1,2,4]triazolo [4,3-a]azepine derivatives were synthesized and screened for their anticonvulsant activities by the maximal electroshock (MES) test, subcutaneous pentylenetetrazol (scPTZ) test, and their neurotoxicity was evaluated by the rotarod neurotoxicity test. The results of these tests showed that 8-heptylamino-5,6- dihydro-4H-benzo[f][1,2,4] triazolo[4,3-a]azepine (7g) was the most promising compound, with median effective dose (ED50) of 19.0 mg/kg, and protective index (PI) value of 14.8 in the MES test, which is much higher than the PI value of the prototype antiepileptic drug carbamazepine (PI = 8.1), phenytoin (PI = 6.9), phenobarbital (PI = 3.2), and sodium valproate (PI = 1.6). The possible structure-activity relationship was discussed.

(1E)-6-Meth­oxy-3,4-dihydro­naphthalen-1(2H)-one O-(p-tolyl­sulfon­yl)oxime

In the title compound, C18H19NO4S, the two benzene rings form a dihedral angle of 68.37 (11)°. One of the C atoms of the fused ring bonded to the N atom displays positional disorder with site-occupation factors of 0.763 (7) and 0.237 (7) and the ring has an envelope conformation with the disordered C atoms located on opposite sides of the plane formed by the other atoms. In the crystal, intermolecular C—H⋯O hydrogen bonds link the molecules to form a two-dimensional supramolecular network. The crystal structure is further stablized by weak intermolecular C—H⋯π interactions.

9-(2-Chloro-benz-yloxy)-6,7-dihydro-2H-benzo[c][1,2,4]triazolo[4,3-a]azepin-3(5H)-one.

In the title molecule, C18H16ClN3O2, the seven-membered ring adopts an envelope conformation with the flap atom deviating by 0.801 (5) Å from the mean plane formed by the remaining non-H atoms. Intermolecular N—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers. The crystal packing also exhibits weak intermolecular C—H⋯N hydrogen bonds and π–π interactions with a short distance of 3.734 (3) Å between the centroids of the aromatic rings of neighbouring molecules.