4-hydroxydithiocoumarin is a valuable organic precursor to architect important heterocycles. The three different reactive nucleophilic sites at the 4-hydroxydithiocoumarins display intriguing regioselectivity in its reaction towards various electro-philes. Previously, 4-hydroxydithiocoumarins...
Synthesis of 3-sulfenyl indole derivatives is achieved through oxidative cross-dehydrogenative coupling reaction. A few such newly synthesized compounds have also exhibited anti-proliferative activity via reactive oxygen species mediated cell damage.
A simple and efficient method for regioselective synthesis of 3-arylquinolines is described from α-aminoacetophenones and trans-β-nitrostyrenes using 20 mol% iodine monobromide as a catalyst in acetonitrile solvent at 80 °C.
We report the reaction behaviour of arylamines with nitroalkenes in the presence of bismuth(iii) triflate (10 mol%) and diacetoxyiodobenzene (10 mol%).
A regioselective synthetic strategy for 6-aryl-8,9-dihydro-benzo[c]phenanthridine-10(7H)-ones (4) is accomplished using a one-pot four-component reaction by fine-tuning of reaction temperature. DMSO is excellently used as a reactant-cum-solvent to introduce carbonyl functionality...
The hitherto unreported 2-aryl-10H-thiochromeno[3,2-b][1,4]oxathiin-10-one derivatives are accomplished in a single pot from 4-hydroxydithiocoumarins, arylacetylenes and dimethyl sulfoxide in the presence of 10 mol% CuI and K2CO3 in an oil-bath at...
An unprecedented metal-free and catalyst-free synthesis of benzo[c]chromeno[4,3,2-gh]phenanthridine derivatives, a class of 1,6-diheterophenalenoid heterocycle, is reported for the first time. The oxidative cross-coupling reaction for the remote cyclization is achieved...
An efficient synthetic protocol for the α-sulfenylation of 1,3-dicarbonyl compounds is reported through a cross dehydrogenative coupling reaction with 4-hydroxydithiocoumarins in the presence of 10 mol% KI and 1 equiv. TBHP in toluene under reflux conditions. Some of the products are utilized for the synthesis of substituted new pyrazole derivatives on reaction with phenylhydrazine in ethanol at room temperature. In addition, α-benzylation is also achieved on treatment with benzyl bromide using K2CO3/CH3CN under mild conditions. The salient features of the present protocol are good yields, mild reaction conditions, shorter reaction time, no byproducts were formed (sulfoxide/sulfone), and no deacylation occurs during the process. In the present protocol, 4-hydroxydithiocoumarin is converted into a suitable electrophile through a radical substitution pathway, which undergoes ultimately C–S bond formation with 1,3-dicarbonyl compounds by a nucleophilic substitution reaction.
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