Synthesis of 2-methylthie no [3,2-b]thieno-[2,3-d]thiazole

A new heterocyclic base — 2-methylthieno[3,2-b]thieno[2,3-d]thiazole — was synthesized by heating 2-acetamido-3-hydroxythieno[3,2-b]thiophene with phosphorus pentasulfide.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1039–1041, August, 1976.     

Action of phosphorus pentasulfide on 5-acetamidothiohydantoins and 4-bromo-5-acetamidopyrazoles

New condensed systems — (5,4-thiazolo)imidazoline-2-thione and pyrazolo[5,4-d]thiazoles -are formed by reaction of phosphorus pentasulfide with 5-acetamidothiohydantoins and 4-bromo-5-acetamido derivatives of pyrazole.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 932–934, July, 1974.     

Synthesis of substituted thieno[2,3-d]thiazoles and indolo[3,2-d]thiazoles

Alkylene-, halo-, and aryl-substituted 2-methylthieno[2,3-d]thiazoles were obtained by the action of phosphorus pentasulfide on the corresponding 2-acetylamino-3-bromo- or 2-acetylamino-3-hydroxythiophenes in an organic solvent with heating. 2-Oximes of halo- and methyl-substituted isatins were converted by reduction and acylation into 2-hydroxy-3-acetylaminoin-doles, from which 2-methylindolo[3,2-d]-thiazoles were obtained by the action of phosphorous pentasulfide with heating in xylene.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 410–417, March, 1987.     

Saturated nitrogen-containing heterocycles VI. Alkyl-2-thiopyrrolidones and their acetyl derivatives

A number of 5-alkyl-2-thiopyrrolidones and 1-methyl-5-alkyl-2-thiopyrrolidones were synthesized by the reaction of the corresponding pyrrolidones with phosphorus pentasulfide. The 5-alkyl-2-thiopyrrolidones were acylated.See [1] for communication V.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 333–335, March, 1972.     

Synthesis of 3-carboxyalkylthia-zolidine-2-thione 4-thiosemicarbazones and their derivatives

3-Carboxyalkylthiazoltdine-2-thion-4-ones react with phosphorus pentasulfide to give 4-thiono analogs, which react with thtosemicarbazide to give the corresponding 4-thiosemicarbazones. 5-Substituted derivatives were obtained by condensation of the oxo compounds with 3-carboxyalkylthiazolidine- 2-thione-4-thiosemicarbazones.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 900–902, July, 1976.     

Synthesis of methyl-substituted thiazole bases with a condensed furan,thiophene, or selenophene ring

Methyl-substituted heterocyclic bases with a furan, thiophene, or selenophene ring condensed with a thiazole ring were synthesized by heating the appropriate o-bromo acetamido derivatives with phosphorus pentasulfide or by oxidation of thioacyl compounds with potassium ferricyanide in alkaline media.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1495–1498, November, 1977.     

Analogs of pyrimidine nucleosides. 13. 1-Substituted 4-thiouracils

4-Thiouracil derivatives with various oxygen-containing groupings as substituents attached to the N₁ atom were obtained by thionation of 1-substituted uracils with phosphorus pentasulfide. It is demonstrated that the yield of the 4-thiouracil derivative depends on the strength of the C-N pseudoglycoside bond in the starting 1-substituted uracil.See [1] for communication 12.Translated from Khimlya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1109–1113, August, 1980.     

The lignin of the algaFucus vesiculosus

Summary 4-Thio analogs of deoxyvasicinone have been synthesized by the reaction of deoxyvasicinone and its derivatives and homologs with phosphorus pentasulfide. The reduction of these thio analogs has given deoxypeganine and its homologs.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 668–670, September, October, 1977.     

Production of alkane and cyclohexane derivatives with two heterocyclic substituents of the furan,pyrrole, and thiophene series

Heating 1,2,11,12-tetrachloro-2,11-bis(R-4,9-dodecanediones) and 1,4-bis(3-R-3,4-dichlorobutanoyl)cyclohexanes gave, respectively, 1,4-difuryl derivatives of butane and cyclohexane, while treatment of them with primary amines or phosphorus pentasulfide in DMF was used to synthesize dipyrryl and dithienyl compounds. 1-R-3-R¹-3,4-Dichlorobutanones react with ethylenediamine in aqueous alkali solutions to give 1,2-dipyrryl or monopyrryl derivatives of ethane.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1185–1189, September, 1991.     

Molecular structure of (3,5-diallylisocyanuratomethyl)bis(chloromethyl)phosphine oxide. Synthesis of (3,5-diallylisocyanuratomethyl)phosphine sulfides

X-Ray study of the (3,5-diallylisocyanuratomethyl)bis(chloromethyl)phosphine oxide showed that the phosphorylmethyl group is bonded to the nitrogen atom of the cycle. Reaction of the tris(chloromethyl)phosphine sulfide with sodium diallylisocyanurate gave (3,5-diallylisocyanuratomethyl)bis(chloromethyl)phosphine sulfide, and treatment of the tris(3,5-diallylisocyanuratomethyl)phosphine oxide with phosphorus pentasulfide gave a tris(3,5-diallylisocyanuratomethyl)bis(chloromethyl)phosphine sulfide.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1446–1448, August, 1993.     

Thionylation of 5-alkyl-3H-furan-2-ones and their non-cyclic 4-oxoalkanoate ester analogs

We have studied thionylation of 5-R-3H-furan-2-ones and 4-oxoalkanoates using phosphorus pentasulfide and the Lawesson reagent. It was found that the structure of the reaction products dependent on the thionylating agent. Preparative methods have been developed for the synthesis of 5-R-5H- and 5-R-3H-thiophen-2-ones and 5-R-3H-furan-2-thiones.N. G. Chernyshevskii State University, Saratov 410600, Russia; e-mail: sorokin@scnit.saratov. su. Translated from Khimiya Geterotsklicheskikh Soedinenii, No. 1, pp. 44–47, January, 1999.     

Chemistry of heteroanalogs of isoflavones

Condensation of 2-pyridylacetonitrile with polyphenols gave the corresponding -(2-pyridyl)-acetophenones, which were converted to the pyridine analogs of natural isoflavones and to 3-pyridylchromones with methyl, trifluoromethyl, and ethoxycarbonyl groups in the 2 position. The antimicrobial activity of 3-pyridylchromones and their reaction with alkylating and acylating agents and phosphorus pentasulfide were investigated.See [1] for communication V.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1180–1185, September, 1977.     

Reaction of 4-Amino-1,2,4-triazines with phosphorus pentasulfide. Deamination during aromatization

Synthesis of several derivatives of thieno[2,3-e]-1,2,4-triazines has been achieved via the action of phosphorus pentasulfide on 6-vinyl- or 6-acylmethyl-5-oxo-1,2,4-triazine derivatives. During these investigations interesting synthetically useful functions for phosphorus pentasulfide in pyridine were observed, among which the deamination of certain N-amino heterocycles is unprecedented.     

Phosphorus pentasulfide and Lawesson reagent in synthesis of 1,3-thiazole-4-thiol derivatives

Available S-amidophenacylation products of thiols and sulfanylphenols on treatment with phosphorus pentasulfide or, which is better, Lawesson reagent convert into the corresponding 1,3-thiazole-4-thiol derivatives that are easily oxidized with hydrogen peroxide. The latter reaction was used to introduce a series of alkyl- or arylsulfonyl groups in the 4 position of the thiazole ring. This general approach significantly extends the limited range of synthetic procedures for 1,3-thiazole-4-thiol derivatives.Translated from Zhurnal Obshchei Khimii, Vol. 74, No. 9, 2004, pp. 1529–1533.Original Russian Text Copyright © 2004 by Belyuga, Brovarets, Drach.This revised version was published online in April 2005 with a corrected cover date.     

Thiazane-2, 4-dithione and its 3-aryl derivatives

Reaction of 2-thiothiazane-4-one and its 3-aryl derivatives with phosphorus pentasulfide in toluene or dichloroethane gives thiazane-2, 4-dithione, or the corresponding 3-aryl derivatives. The compounds are characterized by absorption maxima (or bends) at three bands, 244–262, 315–321, and 339–350 m. The IR spectra exhibit bands at 14.93 (C-S-C), 6.64, and 6.84 (N-C-S), and 7.34, 8.43, 7.14 (CH₂).     

DEOXYGENATION OF SULFOXIDES WITH BORON SULFIDE

Abstract

Among the reagents used for reducing sulfoxides to sulfides there are a number of sulfur-containing compounds /sulfite, mercaptans, carbodithioic acid, mono- and dithiophosphoric acids, sulfinyl chlorides, thionyl chloride, phosphorus pentasulfide/.     

2,6‐Diaryl‐4,4‐disubstituted‐4H‐thiopyran: Source for spiro heterocycles

The 1,5‐diaryl‐3,3‐disubstituted‐1,5‐pentanedione on reaction with ammonium acetate, phosphorus pentoxide and phosphorus pentasulfide gave respective 1,4‐dihydropyridine, 4H‐pyran and 4H‐thiopyran. Novel spiro heterocycles have been obtained by the cyclocondensation of 4H‐thiopyran with hydrazine, hydroxylamine, urea and thiourea.     

The reaction of phosphorus pentasulfide with halogen-substituted nitrogen heterocycles

The novel nucleophilic displacement of halogen by sulfur, by the use of phosphorus pentasulfide in boiling pyridine has been shown to be a general reaction for activated halogen nitrogen heterocycles.     

A novel formation of 1,2,3-butatriene episulfides by thionation of methylenecyclopropanones

Sterically hindered methylenecyclopropanones were thionated with phosphorus pentasulfide in pyridine to afford novel 1,2,3-butatriene episulfides and thiiranoradialene derivative via methylenecyclopropanethione intermediate.     

Novel synthesis of oxa[9]helicenes by Lawesson’s reagent-mediated cyclization of helical quinone derivatives

New oxa[9]helicenes which possess one furan ring have been readily prepared by reactive helical quinone with Lawesson’s reagent or phosphorus pentasulfide in good yields. The versatility of this protocol has been demonstrated with various substituted helical quinones.