Silica‐supported ICl as a novel heterogeneous system for the rapid oxidation of urazoles to triazolinediones

ICl–SiO₂ as a new reactive system was prepared by the treatment of iodine monochloride with an activated silica gel in chloroform. ICl–SiO₂ in a heterogeneous system efficiently oxidized urazoles to the corresponding triazolinediones under mild conditions in high yields at room temperature. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:389–393, 2008; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20444     

N → C2 → C3 migration of the dichlorophosphino group in the synthesis of phosphorylated NH‐pyrroles

A successive N → C₂ → C₃ migration of the dichlorophosphino group has been found to occur in phosphorylation of unsubstituted pyrrole with phosphorus trichloride. As a result of this migration, a number of hitherto unknown C‐phosphorylated N‐unsubstituted pyrroles have been obtained. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:671–676, 2008; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20495     

Facile synthesis of selenocarboxamides from nitriles using Se/CO/H2O under atmospheric pressure

Aromatic and aliphatic nitriles can be conveniently converted into the corresponding selenocarboxamides with Se/CO/H₂O under atmospheric pressure without use of a base. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:211–214, 2008; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20398     

MnCl2‐Promoted synthesis of quinoxaline derivatives at room temperature

MnCl₂ efficiently catalyzes the condensation of o‐phenylenediamine derivatives with 1,2‐diketones at room temperature to afford the corresponding quinoxaline derivatives in high yields. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:218–220, 2008; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20401     

Bismuth triflate catalyzed prins‐type cyclization in ionic liquid: Synthesis of 4‐tetrahydropyranol derivatives

The reaction of aldehydes with homoallylic alcohols in the presence of catalytic amount of bismuth triflate in [bmim]PF₆generates 4‐tetrahydropyranol derivatives in excellent yield and with high diastereoselectivity. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:104–106, 2008; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20403     

A convenient synthesis of 2‐(1H‐1,2,4‐triazol‐1‐yl)‐2H‐1,4‐benzothiazine derivatives

A series of 2‐(1H‐1,2,4‐triazol‐1‐yl)‐2H‐1,4‐benzothiazines were designed and synthesized by condensation of 1,2,4‐triazole‐substituted ω‐bromoacetophenones and o‐aminothiophenols with the aid of K₂CO₃ under mild conditions with moderate to high yields. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:332–336, 2008; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20434     

Palladium N‐heterocyclic‐carbene‐catalyzed ortho‐arylation of benzaldehyde derivatives

New, sterically demanding 1,3‐dialkylbenzimidazolium salts ( 2a–c ) as N‐heterocyclic‐carbene precursors have been synthesized and characterized. The ortho position of aromatic aldehydes was directly and selectively arylated with aryl chlorides in the presence of a catalytic system prepared in situ from Pd(OAc)₂, 1,3‐dialkylbenzimidazolium chlorides ( 2a–c ), and Cs₂CO₃. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:569–574, 2008; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20479     

Cobalt(II) chloride as a novel and efficient catalyst for the synthesis of 1,2,5‐trisubstituted pyrroles under solvent‐free conditions

CoCl₂ is used as an efficient catalyst in the Paal–Knorr condensation of 2,5‐hexadione with primary amines under solvent‐free conditions, leading to the formation of pyrrole derivatives in excellent yield. This method is very easy, rapid, and high yielding reaction for the synthesis N‐substituted pyrrole derivatives. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:592–595, 2008; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20482     

Facile and efficient method for preparation of schiff bases catalyzed by P2O5/SiO2 under free solvent conditions

A simple and convenient method for the preparation of Schiff bases is developed. In this method, the Schiff base compounds were prepared from the reaction of carbonyl compounds with primary amines. In this reaction, P₂O₅/SiO₂ have catalyzed the Schiff base formation in dry media under solvent‐free conditions. Advantages of this method are use of an inexpensive and efficient catalyst, high yields of products, short reaction times, and simpli‐city of the reaction and workup. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:43–47, 2008; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20383     

A convenient synthesis of oxazolidinone derivatives linezolid and eperezolid from (S)‐glyceraldehyde acetonide

A new convenient method for the synthesis of oxazolidinone antibacterials Linezolid and Eperezolid from readily available (S)‐glyceraldehyde acetonide was developed. The key steps include reductive amination of arylamine and (S)‐glyceraldehyde acetonide in the presence of NaBH₄ and 4 Å sieve, followed by hydrolysis and regioselective cyclization. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:316–319, 2008; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20435     

Synthesis,characterization, and biological activity of phosphorylated/thiophosphorylated compounds of 2‐substituted benzimidazoles

A series of phosphorylated and thiophosphorylated compounds of 2‐substituted benzimidazoles have been synthesized by the reaction of POCl₃ and PSCl₃ with 2‐substituted benzimidazoles in different molar ratios. The compounds have been characterized by elemental analyses, infrared, and ¹H NMR and ³¹P NMR spectral studies. These compounds were found to be insecticidal when tested against Periplenata americana. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:154–157, 2008; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20385     

Bismuth‐catalyzed cyclization of amino‐1,6‐enynes

Bi(OTf)₃ effectively catalyzed the cyclization of amino‐1,6‐enynes, leading to bicyclic amine and cyclopentadienyl amino compounds. The selectivity of the products depends on the substitution pattern of the olefinic moiety. ¹⁹F NMR trace experiment of the reaction and other results indicate a novel alkynophilicity of the bismuth species. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:644–648, 2008; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20490     

Synthesis of phosphorous acid and its derivatives based on the reaction of elemental phosphorus (P4) and aqueous solution of choline in the presence of the hydroxides of earth alkali metals

A nonchloric method for the synthesis of phosphorous acid and barium and calcium phosphites is proposed, involving the reaction of elemental phosphorus (P₄) with aqueous barium and calcium hydroxides in the presence of quaternary ammonium base (choline). Conditions for the preparation of high‐purity phosphorous acid based on the oxidation of the hypophosphite ion to the phosphite ion in a strong alkali medium were studied. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:517–519, 2008; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20472     

A stable silagermene (tBu3Si)2Si=Ge(mes)2 (mes = 2,4,6‐trimethylphenyl): Synthesis,X‐ray crystal structure,and thermal isomerization

A stable silagermene, 1,1‐bis(tri‐tert‐butylsilyl)‐2,2‐bis(2,4,6‐trimethylphenyl)silagermene, was synthesized by the reaction of dilithiosilane (^tBu₃Si)₂SiLi₂ with dichlorodimesitylgermane. Its structure was determined by spectroscopic data and X‐ray crystallography, which showed the SiGe length to be 2.2769(8) Å. The silagermene underwent isomerization at 100ˆC to form the corresponding symmetrically substituted isomer (E)‐1,2‐bis(tri‐tert‐butylsilyl)‐1,2‐bis(2,4,6‐trimethylphenyl)silagermene. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:649–653, 2008; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20503     

Interactions of metal‐encapsulated fullerenes with solvents

The present investigation reports on the interaction of M@C₆₀(M = Be, Mg, Ca) with solvents (H₂O, CH₃OH, HF, NH₃) using Density Functional Theory calculations. Our computations reveal that the interaction of the fullerene species increases when endohedral metal atoms are inserted into its cavity. The most profound interaction of the fullerene systems is with water and hydrogen fluoride. © 2008 Wiley Periodicals, Inc. Int J Quantum Chem, 2008     

An efficient one‐pot procedure for the preparation of 1,3,4‐thiadiazoles in ionic liquid [bmim]BF4 as dual solvent and catalyst

The one‐pot three component condensation of hydrazine hydrate with substituted phenylisothiocyanates followed by the addition of substituted benzaldehydes in the presence of ionic liquid 1‐butyl‐3‐methylimidazolium tetrafluoroborate ([bmim]BF₄) and in the absence of any other catalyst under mild condition afforded 1,3,4‐thiadiazoles in excellent yields. The reaction workup is simple, and the ionic liquid was easily recovered from the reaction and reused. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:320–324, 2008; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20432     

Synthesis and crystal structure of some phosphite,thiophosphite, and amidophosphite copper(I) halide complexes

Some Cu(I) halides complexes based on P(III) acid esters,{[(RE)₃PCuBr] (where E = O, N, S); R = n‐Pr, i‐Pr, Et₂N} were obtained and characterized using IR, ³¹P NMR spectroscopy, and single crystal X‐ray diffraction. The comparative structural characteristics of complexes with various donor atoms (E = O, N, S) are analyzed. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:483–489, 2008; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20459     

Facile synthesis of phosphorylated azides in ionic liquids and their use in the preparation of 1,2,3‐triazoles

The facile general synthetic route to azidoalkylphosphonates by the nucleophilic substitution reaction in a series of bromoalkylphosphonates was elaborated, using 1‐butyl‐3‐methylimidazolium hexafluorophosphate ([bmim][PF₆]) as a recyclable reaction medium. These azidoalkylphosphonates were used as intermediates for copper(I)‐catalyzed regioselective 1,3‐dipolar cycloaddition with a variety of alkynes to afford 4‐substituted (1H‐1,2,3‐triazol‐1‐yl)alkylphosphonates as potential drug candidates. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:293–300, 2008; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20420     

Confined space regulated polymerization

The confined space produced during the polymerization has access for all small organic molecules or oligomers with small size to enter this confined space; however, it can prevent the macromolecules with big size from entering. Therefore, the reaction between two branched macromolecules is excluded in A₂+B₃ polymerization system, resulting uncrosslinked branched polymers, and there was no gel point observed throughout the polymerization. © 2008 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 46: 1730–1737, 2008     

Synthesis,characterization, and fluorescence phenomena of 1‐naphthoxy and 1‐naphthylamino substituted cyclotriphosphazenes

The reactions of hexachlorocyclotriphosphazene N₃P₃Cl₆ ( 1 ) with 1‐naphthol and 1‐naphthylamine have been examined. The reaction of 1 with sodium 1‐naphthoxy gave the hexakis(1‐naphthoxy)cyclotriphosphazene ( 2 ) in high yield. Geminal 2,2‐di(1‐naphthylamino)‐4,4,6,6‐tetrachlorocyclotriphosphazene ( 3 ) was obtained from the reaction of 1 with 1‐naphthylamine. The structures of phosphazene derivatives were defined by elemental analysis, FTIR, UV‐‐visible, and ¹H, ¹³C, ³¹P NMR spectroscopy. The fluorescence intensity of the compounds was measured in THF and CH₂Cl₂. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:158–162, 2008; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20400