Erratum: Preparation of size‐controlled In2O3 nanoparticles

The article referenced above was first published online on 7 August 2007 with incorrect pagination; the pagination has now been corrected online and in print. Copyright © 2007 John Wiley & Sons, Ltd.     

Efficient synthesis of 1‐substituted‐4‐phenyl‐1, 4‐dihydro‐5H‐tetrazole‐5‐thione and (1‐phenyl‐1H‐tetrazol‐5‐yl)thioacetyl derivatives

A new and convenient synthesis of a variety of N‐ and S‐substituted tetrazoles has been developed via azide and Mannich reaction methods. Compounds were characterized by elemental analysis, MALDI MS, and ¹H NMR data. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:637–643, 2007; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20353     

Synthesis of 4‐(5‐aryl‐1,3,4‐oxadiazol‐2‐yl)phenyl‐hydrazine derivatives from 3‐(4‐hydrazinocarbonyl‐phenyl)sydnones

The synthesis of potential fluorescent active 4‐(5‐aryl‐1,3,4‐oxadiazol‐2‐yl)phenylhydrazine derivatives was accomplished in three steps. The key step was the dehydration cyclization of 1,2‐diacylhydrazines to form the 1,3,4‐oxadiazole ring by use of acetic anhydride/perchloric acid mixture as the dehydrating agent. The sydnone moiety served as the masked hydrazines, which could be demasked by HCl for further application. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:438–442, 2007; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20318     

An efficient electrochemical method for synthesis of (1h‐1,2,4‐triazol‐3‐ylthio)benzen‐1,2‐diol derivatives

Electrochemical oxidation of catechols ( 1a–c ) has been studied in the presence of 3‐mercapto‐1,2,4‐triazole ( 3 ) as a nucleophile in water/acetonitrile (90/10) solutions. The results revealed that the quinones derived from catechols ( 1a–c ) participate in the Michael addition reactions with anion of 3‐mercapto‐1,2,4‐triazole ( 3 ) and are converted to the corresponding (1H‐1,2,4‐triazol‐3‐ylthio)benzen‐1,2‐diol derivatives ( 4a–c ). © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:644–649, 2007; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20359     

Synthesis of 5‐methyl‐4‐oxo‐2‐(coumarin‐3‐yl)‐N‐aryl‐3,4‐dihydrothieno[2,3‐d]‐pyrimidine‐6‐carboxamides

Possible approaches to synthesis of 5‐methyl‐4‐oxo‐2‐(coumarin‐3‐yl)‐N‐aryl‐3,4‐dihydrothieno[2,3‐d]pyrimidine‐6‐carboxamides 4 have been discussed. It is shown that the preferable approach is cyclization of 2‐iminocoumarin‐3‐carboxamides 1 , utilizing 5‐amino‐3‐methyl‐N²‐arylthiophene‐2,4‐dicarboxamides 2 as binucleophilic reagents. The proposed procedure allowed us to easily obtain 4 in two stages, using common reagents. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:341–346, 2007; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20303     

Synthesis of novel N‐alkyl/aryl‐N′‐(4‐arylthiazol‐2‐yl)‐N″‐xylosyl guanidines

The reaction of 2,3,4‐tri‐O‐acetyl‐β‐D‐xylopyranosyl isothiocyanate ( 1 ) and 2‐amino‐4‐arylthiazoles ( 2 ) gave xylosylthioureas 3 . These thiourea derivatives reacted with alkyl/aryl amine in the presence of HgCl₂ to give a new series of N‐alkyl/aryl‐N″‐(4‐arylthiazol‐2‐yl)‐N″‐xylosyl guanidines 4 . Some of the synthesized guanidines were screened for their biological activity. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:688–694, 2007; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20379     

Syntheses and antimicrobial activities of 4‐aryl‐5‐phenylimino‐3‐S‐(hepta‐O‐acetyl lactosyl)‐1,2,4‐thiadiazolines

A series of 4‐aryl‐5‐phenylimino‐3‐S‐(hepta‐O‐acetyl lactosyl)‐1,2,4‐thiadiazolines have been synthesized by the interaction of S‐(hepta‐O‐acetyl lactosyl)‐1‐arylisothiocarbamides and S‐chloro‐N‐phenyl isothiocarbamoyl chloride. The title compounds were characterized on the basis of elemental analysis and IR, NMR, mass spectral studies. The title compounds exhibited comparable antimicrobial activities against pathogens such as E. coli, S. aureus, P. vulgaris, S. typhi, A. niger, and Candida guilliermondii. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:390–392, 2007; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20310     

Synthesis and characterization of oxime‐bearing hexakis(2‐formylphenoxy)‐phosphazene and its derivatives

Hexakis(2‐formylphenoxy)cyclotri‐phosphazene ( 2 ) was obtained from the reaction of hexachlorocylotriphosphazene ( 1 ) with 2‐hydroxy‐benzaldehyde. Hexakis(2‐[(hydroxyimino)methyl]‐phenoxy)cyclotriphosphazene (3) was synthesized from the reaction of 2 with hydroxlaminehydrochloride in pyridine. Hexasubstituted compounds 4, 5, 6, 8, 9 , and 10 were obtained from the reactions of 3 with methyl iodide, ethyl bromide, allyl bromide, propanoyl chloride, benzoyl chloride, and 4‐methoxybenzoyl chloride, respectively. Disubstituted product 7 was obtained from the reaction of 3 with chloroacetyl chloride. Pure and defined products could not be obtained from the reaction of 3 with acetyl chloride, benzyl chloride, and 2‐chlorobenzoyl chloride. The compounds were characterized by elemental analysis and IR, ¹H, ¹³C, and ³¹P NMR spectroscopy. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:791–797, 2007; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20350     

Peculiar reaction of N2‐acyl derivatives of 2‐aryl‐5‐hydrazino‐1,3‐oxazole‐4‐carbonitriles with the lawesson reagent

Easily accessible N²‐acyl derivatives of 2‐aryl‐5‐hydrazino‐1,3‐oxazole‐4‐carbonitriles react peculiarly with the Lawesson reagent. In addition to thionation, the reaction involves a recyclization to afford new substituted 2‐(5‐amino‐1,3‐thiazol‐4‐yl)‐1,3,4‐thiadiazoles. Their structure is corroborated spectroscopically and by the X‐ray diffraction method. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:782–785, 2007; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20413     

A novel one‐pot procedure for preparation of some new condensed pyrido[2,3‐d]pyrimidine(1H,3H)‐2,4‐diones

A novel one‐pot procedure for preparation of some new condensed pyrido[2,3‐d]pyrimidine(1H,3H)‐2,4‐diones based on condensation of ninhydrin, alkyl cyanoacetate, and 6‐aminouracil derivatives has been reported. The reactions were carried out in refluxed ethanol and were completed in less than 2 h. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:16–18, 2007; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20242     

Construction of a combinatorial library of 2‐(4‐oxo‐4H‐1‐benzopyran‐3‐yl)‐4‐thiazolidinones by microwave‐assisted one‐pot parallel syntheses

A one‐pot liquid‐phase combinatorial synthesis of 2‐(4‐oxo‐4H‐1‐benzopyran‐3‐yl)‐4‐thiazolidinones bearing diverse substituents at the 3‐position under microwave irradiation was successfully performed using 3‐formyl chromone, primary amine, and mercaptoacetic acid as reactants. Compared to an identical library generated by conventional parallel synthesis, the microwave‐assisted parallel synthesis approach dramatically decreased the reaction time from an average of 9 h to 5 min, and substantially increased the product yields. The coupling of microwave technology with liquid‐phase combinatorial synthesis constitutes a novel and particularly attractive avenue for the rapid generation of structurally diverse libraries. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:381–389, 2007; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20309     

Microwave‐assisted synthesis and anti‐HIV activity of new benzenesulfonamides bearing 2,5‐disubstituted‐1,3,4‐oxadiazole moiety

New benzenesulfonamides, most of which are chiral, incorporating 1,3,4‐oxadiazole, and selected amino acid entities have been synthesized, using the microwave irradiation method. Most of the synthesized compounds were tested against HIV activity. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:425–431, 2007; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20316     

Synthesis of α‐fluoro‐β‐trifluoromethyl alka‐2,4‐dienes

The palladium/copper(I) iodide cocatalyzed coupling reaction of (Z)‐α‐fluoro‐β‐trifluoromethylstannanes ( 1 ) with vinyl iodides ( 2 ) has been explored giving substituted α‐fluoro‐β‐trifluoromethyl dienes ( 3 ) in 33–95% yields. In studies we have conducted so far, a larger number of the configurations of the products remained unchanged (cases 3a, 3e–h ), though in several cases (cases 3b–d ) two configurations of the products were obtained. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:208–211, 2007; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20284     

Chemoselective synthesis of thieno[3,2‐c][1,8]naphthyridin‐4(5H)‐ones by tandem cyclization

A number of the thieno[3,2‐c][1,8]‐naphthyridin‐4(5H)‐ones are chemoselectively synthesized from 4‐(4′‐aryloxybut‐2′‐ynylthio)‐1‐phenyl‐1,8‐naphthyridin‐2(1H)‐ones in 82–90% yield by the formation of sulfoxide, followed by [2,3] and [3,3]sigmatropic rearrangement and an intramolecular Michael addition. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:87–92, 2007; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20234     

Original recyclization of S‐phenacyl derivatives of 4‐acylamino‐2‐mercapto‐1,3‐oxazoles and their analogues

Readily accessible acylamino(chloro)acetophenones, if treated with sodium rhodanide and α‐halogenocarbonyl compounds, provide 4‐acylamino‐5‐aryl‐2‐mercapto‐1,3‐oxazole derivatives which undergo recyclization on heating in polyphosphoric acid to give substituted 1,3‐thiazol‐2(3H)‐ones or 1,3‐thiazolidin‐2,4‐diones containing 2‐alkyl(aryl)‐5‐aryl‐1,3‐oxazol‐4‐yl residues at the N³ atom. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:432–437, 2007; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20317     

Synthesis and antimicrobial activity of new functionalized derivatives of [1,2,4]triazolo[4,3‐a]pyrimidin‐5(1H)‐one

New functionalized 1,7‐diaryl‐6‐cyano‐1,2,4‐triazolo[4,3‐a]pyrimidin‐5(1H)‐one derivatives ( 5a–j ) were synthesized via reaction of 5‐cyano‐6‐phenyl‐2‐thiouracil 1 with the respective hydrazonoyl halides 2a–j and their biological activity was evaluated. The mechanism and the regioselectivity of the studied reactions are discussed. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:393–398, 2007; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20311     

Synthesis of some new benzofuran‐based thiophene, 1,3‐oxathiole and 1,3,4‐oxa(thia)diazole derivatives

Treatment of 3‐(3‐methylbenzofuran‐2‐yl)‐3‐oxopropanenitrile ( 1 ) with phenyl isothiocyanate afforded the thioacetanilide derivative 3 , which when reacted with α‐haloketones, α‐halodiketones, and hydrazonoyl chlorides gives thiophene, 1,3‐oxathiole, and 1,3,4‐thiadiazole derivatives 6a,b, 10a,b and 14a–g , respectively. Treatment of 3‐methyl‐2‐benzofurancarboxylic acid hydrazide ( 15 ) with benzaldehyde followed by bromine afforded the 1,3,4‐oxadiazole derivative 18 . Treatment of the acid hydrazide 15 with phenyl isothiocyanate gave the thiosemicarbazide 20 . Compound 20 could be converted into 1,3,4‐oxadiazole, 1,2,4‐triazole‐3‐thione, and 1,3,4‐thiadiazole derivatives 21, 22 , and 23 , respectively. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:294–300, 2007; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20298     

An efficient and green preparation of 9‐arylacridine‐1,8‐dione derivatives

9‐Arylacridine‐1,8‐dione derivatives were prepared in an ionic liquid medium in the presence of CeCl₃ ċ 7H₂O through an one‐pot procedure. The method presented here has the advantages of environmental benignancy, good‐to‐excellent yields, and simple operational procedure. Moreover, the solvent and catalyst can be easily recovered and reused for several runs without obvious loss of activity. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:786–790, 2007; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20410     

Synthesis and characterization of diorganotin(IV) complexes of Schiff bases with ONO‐type donors and crystal structure of [N‐(2‐hydroxy‐4‐nitrophenyl)‐3‐ethoxysalicylideneiminato]diphenyltin(IV)

A series of neutral complexes, namely, [N‐(2‐hydroxy‐4‐nitrophenyl)‐3‐hydroxysalicylideneiminato]‐ diphenyltin(IV) ( Ia ), [N‐(2‐hydroxy‐4‐nitrophenyl)‐3‐methoxysalicylideneiminato]diphenyltin(IV) ( IIa ) and [N‐(2‐hydroxy‐4‐nitrophenyl)‐3‐ethoxysalicylideneiminato]diphenyltin(IV) ( IIIa ) were prepared by the reaction of diphenyltin dichloride on the corresponding Schiff bases. The Schiff bases were the reaction products of 2‐hydroxy‐4‐nitroaniline and appropriate salicylaldehydes. All the compounds were characterized by elemental analysis, ¹H‐NMR, ¹³C‐NMR, IR and mass spectroscopy. Compound IIIa was also characterized by single crystal X‐ray diffraction and shows a C₂NO₂ coordination geometry nearly half‐way between a trigonal bipyramidal and square pyramidal arrangement. In the solid state, π? π interactions exist between the aniline fragments of neighbouring molecules. Copyright © 2007 John Wiley & Sons, Ltd.