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1.
J Org Chem ; 81(23): 11594-11602, 2016 12 02.
Article in English | MEDLINE | ID: mdl-27813414

ABSTRACT

An operationally simple cascade protocol has been developed for the construction of 1,2- and 1,3-dithiole derivatives from α-enolic dithioesters. 1,2-Dithioles are achieved by the reaction of dithioesters with elemental sulfur in the presence of InCl3 under solvent-free conditions. 1,3-Dithioles have been constructed via DABCO mediated self-coupling of dithioesters in open air enabling the formation of two new C-S bonds and one ring in a single operation in contiguous fashion. The reactions proceeded smoothly affording the desired sulfur-rich heterocycles in good to excellent yields, exhibiting gram-scale ability and broad functional group tolerance utilizing easy to handle cheap and easily available reagents. The probable mechanisms for the formation of 1,2- and 1,3-dithioles from α-enolic dithioesters have been suggested.

2.
Dalton Trans ; 43(34): 13096-104, 2014 Sep 14.
Article in English | MEDLINE | ID: mdl-25043803

ABSTRACT

A novel non-enzymatic peroxide sensor has been constructed by using nickel oxide (NiO) thin films as sensing material, which were prepared by a two-step process: (i) electrodeposition of nickel sulfide (NiS) and (ii) thermal air oxidation of as-deposited NiS to NiO. The resultant material is highly porous and comprises interconnected nanofibers. UV-Vis spectroscopy, FTIR spectroscopy, X-ray photoelectron spectroscopy (XPS), X-ray diffraction (XRD) and field-emission scanning electron microscopy (FESEM) were used for a complete characterization of nanostructured NiO thin films. Cyclic voltammetry study shows that NiO/ITO electrode facilitates the oxidation of hydrogen peroxide and exhibits excellent catalytic activity towards its sensing. The amperometric study of NiO/ITO was carried out to determine the sensitivity, linear range, detection limit of the proposed sensor. The sensor exhibits prominent electrocatalytic activity toward the oxidation of H2O2 with a wide linear range and a low detection limit. The possible use of the synthesized NiO thin films as an effective photocatalyst for the decomposition of phenol is also discussed.

3.
J Org Chem ; 76(19): 8009-14, 2011 Oct 07.
Article in English | MEDLINE | ID: mdl-21851110

ABSTRACT

An efficient and experimentally rapid protocol for the synthesis of hitherto unreported 2,3-dicarboalkoxy-4-aroyl/heteroaroyl/alkanoyl thiophenes has been developed via 1-2 (C-S) and 3-4 (C-C) bond connections promoted by 4-dimethylaminopyridine (DMAP). Optimally, the reaction takes only 3-5 min when ß-oxodithioester and dialkyl acetylenedicarboxylate are stirred in DCM at room temperature in the presence of DMAP. This method allows a clean and general synthesis of previously inaccessible and synthetically demanding thiophenes containing the ferrocenyl group. The speed, experimental ease, and high yields of this process are improvements over existing methods to access this important substructure.


Subject(s)
Chemistry Techniques, Synthetic/methods , Thiophenes/chemistry , Thiophenes/chemical synthesis , Kinetics , Pyridines/chemistry
4.
Org Lett ; 13(14): 3762-5, 2011 Jul 15.
Article in English | MEDLINE | ID: mdl-21688790

ABSTRACT

A highly efficient one-pot three-component regioselective synthesis of 4-aryl-3-aroyl-2-methylsulfanyl-4,6,7,8-tetrahydrothiochromen-5-ones has been developed by annulation of ß-oxodithioesters with aldehydes and cyclic 1,3-diketones under solvent-free conditions promoted by P(2)O(5). No cocatalyst or activator is needed in this protocol. The merit of this process is highlighted by its high efficiency of producing three new bonds and a stereocenter in one operation.

5.
J Org Chem ; 75(22): 7785-95, 2010 Nov 19.
Article in English | MEDLINE | ID: mdl-20979420

ABSTRACT

An efficient and highly convergent route to dihydropyrimidinones (DHPMs) and hitherto unreported dihydropyridopyrimidinones has been developed by one-pot, three-component cyclocondensation of aromatic aldehydes, ß-oxodithioesters, and urea/6-amino-1,3-dimethyluracil in the presence of recyclable SiO2-H2SO4. On the other hand, salicylaldehyde, ß-oxodithioester, and urea reacted under similar conditions to afford the 3-aroyl/heteroaroyl-2H-chromen-2-thiones in high yields instead of Biginelli product. The attractive feature of this approach is the synthesis of three important bioactive heterocyclic frameworks from the same ß-oxodithioester under the similar reaction conditions, making this new strategy highly useful in diversity-oriented synthesis (DOS).


Subject(s)
Coumarins/chemistry , Coumarins/chemical synthesis , Heterocyclic Compounds/chemistry , Heterocyclic Compounds/chemical synthesis , Pyrimidinones/chemistry , Pyrimidinones/chemical synthesis , Sulfhydryl Compounds/chemistry , Sulfhydryl Compounds/chemical synthesis , Uracil/analogs & derivatives , Catalysis , Magnetic Resonance Spectroscopy , Molecular Structure , Uracil/chemistry
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