Thiosemicarbazides and Thiosemicarbazones

Thiazoies from a-Halocarbonyl Compounds and Derivatives 249 D. Thiosemicarbazides and Thiosemicarbazones 

General Synthetic Methods for Thiazole and Thiazolium Saits 

When the 5-position is substituted no rearrangement occurs. Phenacylbromide and its substituted derivatives seem to give only products of type 147, in which Rj aryl (517). 

Several sulfonamides (142), Rj = p-H2NS02CeH4, have been obtained by condensing the corresponding thiosemicarbazide (141), R, = p-H2NSO2C6H4, with a-halocarbonyl compounds (396, 466) in alcohol solution. 

R 11-21 2-HYDRAZINOTHIAZOLES FROM THIOSEMICARBAZIDES AND a-HALOCARBONYL COMPOUNDS 

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A very comprehensive review by Campbell133 on the coordination chemistry of thiosemicarbazide and thiosemicarbazones provides details of the thermodynamic, structural, magnetic and vibration-... 

Lukovits, I., A. Shaban, and E. Kalman, Thiosemicarbazides and thiosemicarbazones Non-linear quantitative stiricture-efficiency model of corrosion inhibition. Electrochimica Acta, 2005.50(20) p. 4128-4133. 

With thiosemicarbazides and thiosemicarbazones With thiosemicarbazides [Cu(OH) 2,4,l-0 C6H3(C0NH2)NHNHCS 300 1.77. -Gouy square planar coordination suggested 74S56... 

Monosubstituted thioureas give, in this reaction, a mixture of the isomeric 2-imino-4-thiazolidinones (196) and (197), the former predominating. Similarly, dithiocarbamates, thiocarbamates, thiosemicarbazides, and thiosemicarbazones give analogous 4-thiazolidinones of type (198) and (199), which were further studied. ... 

Synthesis of 2-heterocyclic thiosemicarbazones can be summarized in three reaction sequences following the lead of Klayman et al. [5]. Condensation of equimolar quantities of a thiosemicarbazide and a 2-heterocyclic aldehyde or ketone in an alcoholic solvent is represented by Eq. (1). The product s superscripts refer to positions of substitution in the thiosemicarbazone moiety in accord with lUPAC. 

A great number of nickel complexes with thiosemicarbazide (432) and thiosemicarbazone (433) ligands and their substituted derivates have been examined. Thiosemicarbazone chemistry is... 

In order to investigate the antitubercular activity of thiophene analogs, thiosemicarbazones were synthesized 12). It was found that the addition of a small amount of acetic acid facilitated the reaction between thiosemicarbazide and the thiophene carbonyl compound and that the reaction was essentially completed in one half to one hour. The activities of these semicarbazones, however, were not recorded. 

Thiosemicarbazides (TSC) and thiosemicarbazones generally react with transition metal ions to form chelate complexes by bonding through both the sulfur and the hydrazinic nitrogen atoms. With silver(I) however, they appear to behave as monodentate ligands and bond through the sulfur atom only.436... 

There is a report that describes the isolation of several complexes of ReIV (and of Rev) with thiosemicarbazide and its derivatives. These are obtained by the reactions of [ReCl6]2-, and the so-called a-ReCl4, with thiosemicarbazide and the thiosemicarbazones of acetone, quinolineal-dehyde and 5-chlorosalicylaldehyde.299 While the thiosemicarbazide complex is paramagnetic, in accord with its being an ReIV species, the structural formulation proposed for this complex (and for others of its kind) is based primarily upon IR spectroscopic data and should therefore be regarded as highly speculative. 

Oxystarch reacted with phenylhydrazine to give a yellow compound" " which contained one basic group per dialdehyde unit." Similar reactions were found with isonicotinoylhydrazine, thiosemicarbazide, and p-aminobenzaldehyde thiosemicarbazone. Structures of the general type (97) were assigned to these polymers." That this structure is incorrect for the phenylhydrazine derivative was shown by its formation of a poly(di-phenylformazan). Mester therefore suggested structure (104) for the... 

Horse heart cytochrome c (Sigma, type VI) was purified by chromatography on a Whatman CM-32 column at 4 C as described previously 24 according to the literatures 28 Pyridine aldehyde thiosemicarbazones (PATS) and benzaldehyde thiosemicarbazone (BATS) were synthesized from thiosemicarbazide and corresponding aldehydes , and recrystallized from ethanol. All other reagents were of analytical grade, and used as received. 

Virus replication comprises numerous biochemieal transformations that might provide suitable targets for antiviral therapy. The antiviral effect of thiosemicarbazones was first demonstrated by Hamre et al. [53, 54], who showed that p-aminobenzaldehyde-3-thiosemicarbazone and several of its derivatives were active against vaccinia virus in mice. These studies were extended to include thiosemicarbazones of isatin, benzene, thiophene, pyridine, and quinoline derivatives, which also showed activity against vaccinia-induced encephalitis. The nature of the aldehyde/ketone moiety was not as significant as the presence of the thiosemicarbazide side chain the latter was deemed essential for antiviral activity. 

Ni11 complexes of thiosemicarbazones derived from p-fluorobenzaldehyde and differently substituted thiosemicarbazides (434, 435) are square planar [NiL2] species with the S and hydrizine-N atoms in tram position to each other and a slight tetrahedral distortion in some cases.1235,1236... 

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