Synthesis of N‐aryl S‐alkylthiocarbamates

Several N‐aryl S‐alkylthiocarbamates were synthesized by reactions of isocyanates with LiAlHSH and then with alkyl halides. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:374–378, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10163     

Convenient synthesis of bisphosphonomethylphosphoric acid

The reaction of phosgene or triphosgene with trimethylsilyl dialkylphosphites led to bisdialkylphosphonomethyl‐dialkylphosphates in good yields. The cleavage of the allyl ester was carried out under mild conditions using the Wilkinson catalyst. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:111–113, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10105     

Studies on reactivity of ketosulfones

The cycloaddition of diazomethane, cyclocondensation of hydrazine hydrate, and cyclopropanation of TMSOI to 1‐aroyl‐2‐styrylsulfonylethenes were studied and different novel products thereby obtained were characterized with spectral parameters. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:155–159, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10117     

Selective phosphorylation of dihydroquercetin with trivalent phosphorus reagents

Characteristic features of phosphorylation of dihydroquercetin with trivalent phosphorus reagents were studied. Preparative methods for regioselective phosphorylation were found. The most important chemical properties of dihydroquercetin phosphites and cyclophosphites were studied. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:399–403, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10115     

A facile approach to phosphonic acid diesters

The symmetric H‐phosphonates of carbohydrate and other compounds were conveniently prepared by direct transesterification of the corresponding monohydroxylic compounds with diphenyl phosphite. The approach has the merits of mild reaction conditions and high yields. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:208–210, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10130     

Theoretical and synthetic approach to novel spiroheterocycles derived from isatin derivatives and L‐proline via 1,3‐dipolar cycloaddition

A cyclic secondary α‐amino acid, viz. L ‐proline, reacts with isatin derivatives via decarboxylative azomethine ylide formation and subsequent cycloaddition with various dipolarophiles to give cycloadducts in moderate to good yield. Theoretical studies have been performed to study the stereochemistry of the products formed. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:36–41, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10063     

Reaction of nitrile oxides with vinylphosphonate: A facile,regioselective approach to 5‐phosphonyl‐4, 5‐dihydroisoxazoles

A series of 5‐phosphonyl‐4,5‐dihydroisoxazoles was synthesized from nitrile oxides and diethylvinylphosphonate under very mild conditions in good yields. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:254–257, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10136     

Conversion of 2(3H)‐furanones into 1,3,4‐oxadiazoles

A series of 2‐phenyl‐5‐alkenyl‐1,3,4‐oxadiazoles were synthesized in high yields from the corresponding dicarbonylhydrazides through cyclodehydration. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:570–574, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10197     

Cycloaddition of nitrile oxides to substituted vinylphosphonates

Cycloaddition of nitrile oxides to substituted vinylphosphonates was performed. A series of 4,5‐dihydroisoxazoles containing phosphonyl group were synthesized under very mild condition in excellent regiospecificity. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:309–311, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10149     

Oxidative cyclization in the synthesis of 5‐ and 6‐membered N,O‐heterocycles

The versatility and potential of oxidative cyclization in the synthesis of 5‐ and 6‐membered N‐ and/or O‐heterocycles is presented through judiciously selected examples.© 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:642–670, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10200     

Novel cyclization of dimeric dianions of anils or aldehydes with triphosgene: A safe and efficient synthesis of substituted imidazolidin‐2‐ones and 4,5‐diaryl‐1,3‐dioxolan‐2‐ones

The reaction of Schiff bases or aldehydes with samarium diiodide in dry THF, followed by addition of triphosgene, gives substituted imidazolidin‐2‐ones and 4,5‐diaryl–1,3‐dioxolan‐2‐ones, respectively, in moderate to good yields under mild conditions. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:46–49, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10065     

Photodesulfurization of 2,4‐diaryl‐1,2, 4‐triazole‐3‐thiones

Irradiation of triazole thiones in thin‐film reactor furnished the corresponding desulfurized triazoles in good yield. The required triazole thiones were synthesized from the respective acid hydrazide and isothiocyanate. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:269–272, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10140     

Syntheses of cyanoselenoamides and diselenoamides: Conversion into selenazoles and selenazines

Reactions of dicyano compounds with a potassium selenocarboxylate afforded the corresponding cyanoselenoamides and diselenoamides in good yields of experimentally determined ratios. The obtained cyanoselenoamides were allowed to react with potassium selenocarboxylate, again to afford the corresponding diselenoamides in higher yields. The cyanoselenoamides and diselenoamides were investigated as substrates for preparations of selenazoles and selenazines. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:106–110, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10111     

Asymmetric borane reduction of prochiral ketones catalyzed by phosphinamides prepared from L‐serine

Synthesis of several new chiral phosphinamide catalysts with a proximal hydroxyl group from L ‐serine was described. These compounds have been successfully used in the asymmetric catalytic borane reduction of prochiral ketones. The optically active secondary alcohols were obtained with an enantiomeric excess (ee) up to 81% and excellent yields. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:288–291, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10145     

Cycloaddition of bis‐1,3‐dipolar reagents to 1,3‐diarylprop‐2‐en‐1‐ones

Bis pyrazolines and isoxazolines were prepared by 1,3‐dipolar cycloaddition of benzene‐1,3/1,4‐dicarboxaldehyde dihydrazones and dioximes to 1,3‐diaryl‐prop‐2‐en‐1‐ones. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:379–383, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10169     

Facile synthesis of 2‐alkylthio‐5‐phenylmethylene‐4H‐imidazol‐4‐ones

2‐Alkylthio‐5‐phenylmethylidene‐4H‐imidazol‐4‐ones 4 were synthesized by S‐alkylation of 2‐thioxo‐3‐alkyl(aryl)‐4‐imidazolidinones 3 , which were obtained via cyclization of isothiocyanates 2 with aliphatic(aromatic) primary amines. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:348–351, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10160     

Synthesis of novel thia‐oxadiazolophanes

The novel thia‐1,3,4‐oxadiazolophanes were synthesized regioselectively from 1,4‐bis(5‐mercapto‐1,3,4‐oxadiazol‐2‐yl)butane and various 1,ω‐dihaloalkanes in presence of potassium hydroxide. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:273–275, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10141     

Utility of a 2‐aminothiophene‐3‐carboxamide in the synthesis of thienopyridines and thienopyrimidines

2‐Amino‐4,5,6,7‐tetrahydrobenzo[b]‐ thiophene‐3‐carboxamide ( 1 ) was prepared according to Gewald procedure. Its reactivity toward a variety of chemical reagents was studied to give thienopyridines and ‐pyrimidines. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:459–467, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10179     

C‐phosphorylated pyrrolylcarbaldehydes

Application of N,N‐dimethylhydrazone protective group for synthesis of C‐phosphorylated aldehydes of the pyrrole series was studied. Removal of the hydrazone protection in monophosphorylated pyrrolylcarbaldehyde hydrazones occurs smoothly, while in biphosphorylated derivatives it results in nitrile formation. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:258–261, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10137     

A Stepwise one‐pot synthesis of aryl N‐phosphonamidothionate derivatives of nucleosides

Novel aryl N‐phosphonamidothionate derivatives of nucleosides as membrane‐soluble prodrugs of bioactive free nucleotides have been prepared by phosphochloridothioate chemistry. Unprotected nucleosides, for example uridine and adenosine, were used; phosphorylation took place selectively at the 5′‐position. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:62–66, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10080