- Mechanistic investigation and DFT calculation of the new reaction between S-methylisothiosemicarbazide and methyl acetoacetate
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A study on the synthesis and mechanistical aspects of formation of 3-methyl-5-oxo-3-pyrazolin-1-carboxamide (MOPC) starting from S-methylisothiosemicarbazide hydrogen iodide and methyl acetoacetate was performed. In the alkaline aqueous solution, the intermediate methyl acetoacetate S-methylisothiosemicarbazone undergoes substitution of CH 3S- anion by hydroxide anion, cyclization, carbanion formation, and elimination of methanol, thus yielding corresponding Na-enolate salt of pyrazol-5-one derivative. The structure of the compound obtained after protonation of the formed enolate salt was determined by means of spectroscopic techniques and single-crystal X-ray diffraction analysis. The mechanism of conversion of methyl acetoacetate S-methylisothiosemicarbazone into MOPC was investigated by means of the B3LYP functional, and it was found that the reaction is thermodynamically controlled.
- Markovic, Violeta,Markovic, Svetlana,Janicijevic, Ana,Rodic, Marko V.,Leovac, Vukadin M.,Todorovic, Nina,Trifunovic, Snezana,Joksovic, Milan D.
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- Structure-activity relationships of lipopolysaccharide sequestration in guanylhydrazone-bearing lipopolyamines
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The toxicity of Gram-negative bacterial endotoxin (lipopolysaccharide, LPS) resides in its structurally highly conserved glycolipid component called lipid A. Our major goal has been to develop small-molecules that would sequester LPS by binding to the lipid A moiety, so that it could be useful for the prophylaxis or adjunctive therapy of Gram-negative sepsis. We had previously identified in rapid-throughput screens several guanylhydrazones as potent LPS binders. We were desirous of examining if the presence of the guanylhydrazone (rather than an amine) functionality would afford greater LPS sequestration potency. In evaluating a congeneric set of guanylhydrazone analogues, we find that C16 alkyl substitution is optimal in the N-alkylguanylhydrazone series; a homospermine analogue with the terminal amine N-alkylated with a C16 chain with the other terminus of the molecule bearing an unsubstituted guanylhydrazone moiety is marginally more active, suggesting very slight, if any, steric effects. Neither C16 analogue is significantly more active than the N-C16-alkyl or N-C16-acyl compounds that we had characterized earlier, indicating that basicity of the phosphate-recognizing cationic group, is not a determinant of LPS sequestration activity.
- Wu, Wenyan,Sil, Diptesh,Szostak, Michal L.,Malladi, Subbalakshmi S.,Warshakoon, Hemamali J.,Kimbrell, Matthew R.,Cromer, Jens R.,David, Sunil A.
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Read Online
- Selenium-containing heterocycles from isoselenocyanates: Synthesis of 5-amino-2,4-dihydro-3H-1,2,4-triazole-3-selones
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The reaction of S-methylisothiosemicarbazide hydroiodide (=S-methyl hydrazinecarboximido-thioate hydroiodide; 1), prepared from thiosemicarbazide by treatment with MeI in EtOH, and aryl isoselenocyanates 5 in CH 2Cl2 affords 3H-1,2,4-triazole-3-selone derivatives 7 in good yield (Scheme 2, Table 10). During attempted crystallization, these products undergo an oxidative dimerization to give the corresponding bis(4H-1,2,4-triazol-3-yl) diselenides 11 (Scheme 3). The structure of 11a was established by X-ray crystallography.
- Sommen, Geoffroy L.,Linden, Anthony,Heimgartner, Heinz
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- TRIAZOLE-PYRIDINYL SUBSTITUTED AZACYCLOHEXYL ACETIC ACID COMPOUNDS AS LPA RECEPTOR ANTAGONISTS
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This application relates to novel substituted azacyclohexyl acetic acid compounds, their manufacture, pharmaceutical compositions comprising them, and their use as medicaments for treating a disease associated with dysregulation of lysophosphatidic acid receptors (LPA).
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Paragraph 0465
(2022/02/28)
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- Synthesis and antioxidant activities of new nickel(II) complexes derived from 4-benzy-loxysalicylidene-S-methyl/propyl thiosemicarbazones
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Six nickel(II) complexes of the N2O2chelating thiosemicarbazones were synthesized using N1-4-benzyloxysalicylidene-S-methyl/propyl thiosemicarbazone and methoxy-substitute-salicylaldehydes in the presence of Ni(II) ion by template reaction. The structures of thiosemicarbazones and nickel(II) complexes were characterized by elemental analysis, UV-Vis, IR, and 1H-NMR spectroscopies. The structure of the N1-4-benzyloxysalicylidene-S-propyl thiosemicarbazone (2) was determined by X-ray single-crystal diffraction method. The total antioxidant capacities of synthesized compounds were evaluated by using cupric reducing antioxidant capacity (CUPRAC) method. The thiosemicarbazones exhibited more potent antioxidant capacity than Ni(II) complexes. Trolox equivalent antioxidant capacity (TEAC) of 1c was found highest in tested nickel(II) complexes. In addition, antioxidant activities of tested compounds were evaluated by using the hydroxyl radical, DPPH radical, and ABTS radical scavenging abilities of these compounds.
- Eglence-Bakir, Songül
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p. 835 - 844
(2021/07/26)
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- S-alkylated thiosemicarbazone derivatives: Synthesis, crystal structure determination, antimicrobial activity evaluation and molecular docking studies
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Increasing antimicrobial resistance is one of the most serious threats to human health worldwide. Therefore, there is an urgent need for the discovery of novel antimicrobial agents. Herein, we presented the synthesis of ten thiosemicarbazone derivatives (T1-T10) obtained by the reaction of S-alkylthiosemicarbazide with various dicarbonyl derivatives. The compounds were characterized by IR, 1H NMR, ESI-MS and X-ray crystallography. Reaction with the dicarbonyl compound bearing the 4-fluorobenzoyl group unexpectedly gave a pyrazole derivative (T8) containing the entire S-methylthiosemicarbazone backbone. We extensively screened these derivatives for their antimicrobial activities against Mycobacterium tuberculosis and various bacterial and Candida strains. Additionally, the biofilm inhibition capacity of T8 was evaluated on Staphylococcus epidermidis and Pseudomonas aeruginosa biofilm positive strains. To find out the potential mechanism of anti-biofilm activity against PAO1, the docking studies of T8 were carried out into the binding site of LasR, which is the main regulator of bacterial cell-to-cell communication system known as quorum sensing.
- ?zkul, Ceren,ülküseven, Bahri,?ahin, Onur,Gündüz, Miyase G?zde,Kaya, Bü?ra,Rekha, Estharla Madhu,Sriram, Dharmarajan
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- New M(II) (M=Mn, Co, Ni, Cu, Zn, Pd) coordinative compounds with 2-formylpyridine S-methyl-isothiosemicarbazide
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The synthesis and structure of the new organic proligand 2-formylpyridine S-methyl-isothiosemicarbazone in a bi-protonated form (HL.2HCl) and its coordination compounds with Mn(II) - [Mn(HL)·Cl2], Co(III) - [CoL2]·ClO4, Ni(II) - [Ni(HL)2]·2ClO4, Cu(II) - [Cu(HL)Cl2]·(H2O), Zn(II) - [Zn(HL)2]·2(ClO4)·(H2O) and Pd(II) - [Pd(HL)·Cl]·Cl are reported. According to the X-ray investigation, the ligand has the molecular form of HL in the case of Mn(II), Cu(II), Zn(II) and Pd(II) compounds, and the deprotonated form L? in case of the Co(III) complex. The ligand coordinates to the metal ions via a N,N,N set of donors atoms in case of Zn(II), Cu(II) and Co(III). For Mn(II), the ligand coordinates via N,N donor atoms, whereas in the case of Pd(II) metal ions, the coordination sphere is N,N,S. This latter coordination mode (via S(CH3)) has been previously reported in case of salicylaldehyde S-alkyl-isothiosemicarbazones.
- Danac, Ramona,Pui, Aurel,Corja, Ion,Amarandi, Roxana-Maria,Ciobanu, Catalina Ionica,Apostu, Mircea-Odin,Palamarciuc, Oleg
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- Comparison of non-covalent interactions and spectral properties in 1-methyl-3-methylthio-5-phenyl-1,2,4-triazinium mono- and tetraiodide crystals
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The reaction of 1-methyl-3-methylthio-5-phenyl-1,2,4-triazinium (MTPT) iodide with diiodine in a solution leads to monoiodide crystal structure that in excess of iodine gives the unusual tetraiodide anion with two central iodine atoms in disorder. The bonding within the anion has been characterized as I–…I2…I–; the existence of the bound iodine molecule inside has been proven by the characteristic band in experimental and calculated Raman spectra. Non-covalent interactions of MTPT in considered crystal structures are different. Monoiodide anion as a strong electron donor allows the formation of the S…I chalcogen bonds that are absent in tetraiodide structure. The features of halogen bonds within the I4 2– anion are?also performed.
- Yushina, Irina D.,Rudakov, Boris V.,Stash, Adam I.,Bartashevich, Ekaterina V.
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p. 1981 - 1991
(2019/07/17)
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- Synthetic Route Design of AZD4635, an A2AR Antagonist
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The AstraZeneca approach to synthetic Route Design is exemplified through our AZD4635 chemical development program. The identification of possible new route concepts is presented, as well as their subsequent prioritization for practical exploration based on project objectives. Selected ideas were tested to demonstrate proof of concept for the bond formation strategy and, where successful, were fed into a decision tool based on key SELECTion principles.
- Littleson, Mairi M.,Campbell, Andrew D.,Clarke, Adam,Dow, Mark,Ensor, Gareth,Evans, Matthew C.,Herring, Adam,Jackson, Bethany A.,Jackson, Lucinda V.,Karlsson, Staffan,Klauber, David J.,Legg, Danny H.,Leslie, Kevin W.,Morav?ík, ?tefan,Parsons, Chris D.,Ronson, Thomas O.,Meadows, Rebecca E.
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p. 1407 - 1419
(2019/08/12)
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- 1,3,4-Thiadiazole Compounds and Their Use in Treating Cancer
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A compound of Formula (I): or a pharmaceutically acceptable salt thereof, where: Q can be 1,2,4-triazin-3-yl, pyridazin-3-yl, 6-methylpyridazin-3-yl, or 6-fluoropyridazin-3-yl; R1 can be hydrogen, methoxy, trifluoromethoxy, oxetan-3-yl, 3-fluoroazetidin-1-yl, 3-methoxyazetidin-1-yl, or 3,3-difluoroazetidin-1-yl; R2 can be hydrogen or fluoro; R3 can be hydrogen or methoxy; and R4 can be methoxy, ethoxy, or methoxymethyl; provided that when R1 is hydrogen, methoxy or trifluoromethoxy, then R3 is not hydrogen, and/or R4 is methoxymethyl. The compound of formula (I) can inhibit glutaminase, e.g., GLS1.
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Paragraph 0296; 0297
(2017/06/30)
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- Synthesis of 3-(Alkylamino)-, 3-(Alkoxy)-, 3-(Aryloxy)-, 3-(Alkylthio)-, and 3-(Arylthio)-1,2,4-triazines by Using a Unified Route with 3-(Methylsulfonyl)-1,2,4-triazine
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In our attempts to synthesize 3-(alkylthio)- and 3-(alkoxy)-1,2,4-triazines without substituents at the 5- or 6-position, the synthesis of their anticipated precursor 3-(methylsulfonyl)-1,2,4 triazine was also optimized. The reactivity of 3-(methylsulfonyl)-1,2,4-triazine towards alkyl and aryl thiols, primary and secondary alkylamines, phenols, and alcohols was explored, and the reactions were optimized to maximize the isolation of the corresponding 3-substituted 1,2,4-triazine. Good yields were obtained for the products of the reactions with all of the aforementioned nucleophiles, with the exception of alcohols, by using alkali metal carbonates. Higher yields of 3-(alkoxy)-1,2,4-triazines were obtained by using the appropriate magnesium alkoxide as the nucleophile.
- Shi, Da-Hua,Harjani, Jitendra R.,Gable, Robert W.,Baell, Jonathan B.
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p. 2842 - 2850
(2016/07/07)
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- PYRIDOXAL AMINOGUANIDINE DERIVATIVES AND THEIR SALTS AND PRODUCTION METHOD THEREOF
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PROBLEM TO BE SOLVED: To provide compounds which are good in absorptivity on oral administration, serve as hypoglycemic agents with high safety and are useful as inhibitors for AGE formation reactions and their production method. SOLUTION: A method of producing pyridoxal/aminoguanidine derivatives and their salts having a structure with the amino group of pyridine derivatives of formula (V) substituted with another group comprises reacting pyridoxal with one of 1-amino-3-propyl guanidine hydroiodide, 4-methyl-S-methylisothiosemicarbazide hydroiodide, 3-methylisosemicarbazide hydrochloride and morpholine-4-carboxyimide hydrazide hydroiodide. COPYRIGHT: (C)2015,JPO&INPIT
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Paragraph 0023; 0024
(2019/01/04)
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- Ruthenium(III) S-methylisothiosemicarbazone Schiff base complexes bearing PPh3/AsPh3 coligand: Synthesis, structure and biological investigations, including antioxidant, DNA and protein interaction, and in vitro anticancer activities
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New Ru(III) isothiosemicarbazone complexes [RuCl(EPh3)L 1-4] (E = P or As) were obtained from the reactions between [RuCl3(EPh3)3] and bis(salicylaldehyde)-S-methylisothiosemicarbazone (H2L 1-3)/bis(2-hydroxy-naphthaldehyde)-S- methylisothiosemicarbazone (H2L4) ligands. The new complexes were characterized by using elemental analyses and various spectral (UV-Vis, IR, 1H NMR, FAB-Mass and EPR) methods. The redox properties of the complexes were studied by using cyclic voltammetric method. The new complexes were subjected to various biological investigations such as antioxidant assays involving DPPH radical, hydroxyl radical, nitric oxide radical and hydrogen peroxide, DNA/protein interaction studies and in vitro cytotoxic studies against human breast cancer cell line (MCF-7). New complexes showed excellent free radicals scavenging ability and could bind with DNA via intercalation. Protein binding studies using fluorescence spectroscopy showed that the new complexes could bind strongly with bovine serum albumin (BSA). Photo cleavage experiments using DNA of E-coli bacterium exhibited the DNA cleavage ability of the complexes. Further, the in vitro anticancer activity studies on the new complexes against MCF-7 cell line exhibited the ability of Ru(III) isothiosemicarbazone complexes to suppress the development of malignant neoplastic disease cells.
- Prakash, Govindan,Manikandan, Rajendran,Viswanathamurthi, Periasamy,Velmurugan, Krishnaswamy,Nandhakumar, Raju
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- Theoretical study on structural and mechanistic aspects of synthesis of a 3-aminopyrazole derivative
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The structure of 5-hydroxy-3,5-dimethyl-1-S-methylisothiocarbamoyl-2- pyrazolinium iodide (HDMCPI), a cyclic intermediate for a 3-aminopyrazole derivative, was determined by means of X-ray analysis and spectroscopic techniques. In a treatment of HDMCPI in alkaline aqueous solution, 4-acetyl-3(5)-amino-5(3)-methylpyrazole (AAMP) was unexpectedly yielded. The reaction of HDMCPI was monitored by 1H and 13C NMR spectroscopy. It was shown that keto-imine tautomer appears as the only tautomeric form. Density functional theory explained the spontaneous formation of keto-imine tautomer, whose existence is the main condition for generating a carbanion in alkaline medium. The carbanion further undergoes cyclization and elimination of MeSH, thus yielding AAMP. In the reaction of acetylacetone with thiosemicarbazide instead of S-methylisothiosemicarbazide, there were no traces of AAMP. This result can be attributed to the absence of keto-imine form in the tautomeric equilibrium, which would provide the formation of a carbanion for a nucleophilic attack and further cyclization.
- Markovi?, Svetlana,Joksovi?, Milan D.,Bombicz, Petra,Leovac, Vukadin M.,Markovi?, Violeta,Joksovi?, Ljubinka
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experimental part
p. 6205 - 6211
(2010/10/02)
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- 3-Alkylthio-1,2,4-triazine dimers with potent antimalarial activity
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We report on the discovery of 3-alkylthio-1,2,4-triazine dimers that are potently toxic to Plasmodium falciparum, with single digit nanomolar activity, and up to several thousand-fold lower toxicity to mammalian cells. They are equipotent against chloroquine-resistant strains of P. falciparum.
- Ban, Kung,Duffy, Sandra,Khakham, Yelena,Avery, Vicky M.,Hughes, Andrew,Montagnat, Oliver,Katneni, Kasiram,Ryan, Eileen,Baell, Jonathan B.
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supporting information; experimental part
p. 6024 - 6029
(2010/11/05)
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- Compounds, Compositions and Methods Comprising Triazine Derivatives
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The present invention relates to compositions and methods for treating a disease in an animal, which disease is responsive to inhibiting of functional cystic fibrosis transmembrane conductance regulator (CFTR) polypeptide by administering to a mammal in need thereof an effective amount of a compound defined herein (including those compounds set forth in Table 1 or encompassed by formulas I-II) or compositions thereof, thereby treating the disease. The present invention particularly, relates to a method of treating diarrhea and polycystic kidney disease.
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Page/Page column 71
(2009/10/30)
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- HETEROAROMATIC COMPOUNDS HAVING SPHINGOSINE-1-PHOSPHATE (S1P) RECEPTOR AGONIST BIOLOGICAL ACTIVITY
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A novel compound having agonist activity at the S1P3 receptor which is represented by the formula I wherein X is selected from the group consisting of CR3, N and NO;Y is selected from the group consisting of CR3, N and NO;Z is selected from the group consisting of CR3, N and NO; and at least one of X, Y and Z is N or NO; V is O or NOR4 R1 is an aryl group;R2 is an aryl group;R3 is selected from the group consisting of H and alkyl; and 2 of said R3 groups may together form a cyclic alkyl ring having from 3 to 6 carbon atoms; R4 is selected from the group consisting of H and alkyl;a is 0 or an integer of from 1 to 6;b is 0 or 1;c is 0 or 1;f is 0 or an integer of 1 or 2;x is 0 or 1;y is 0 or an integer of from 1 to 3; andz is 0 or an integer of from 1 to 3.
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(2008/06/13)
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- TRIAZINE DERIVATIVES, THEIR PREPARATION AND THERAPEUTIC APPLICATION THEREOF
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The invention relates to triazine derivatives of general formula (I): Wherein R1, R2 and R3 are as defined herein. The invention also relates to a method for preparing these triazine derivatives and to the therapeutic application thereof.
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Page/Page column 8
(2008/06/13)
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- MODULATORS OF PERIPHERAL 5-HT RECEPTORS
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Novel modulators of 5-HT4 receptors have been developed which have a selectivity for peripheral receptors rather than those of the central nervous systems. Theses include novel derivatives of known modulators as well as entirely novel entities. Surprisingly, the derivatised compounds of the known modulators maintain a high binding affinity to 5-HT4 receptors, despite the presence of an acidic moiety at the end of an optional chain. The entirely novel entities also exhibit good binding affinity to 5-HT4 receptors. All of the compounds of the invention have a common motif which includes a basic nitrogen moiety and an acidic moiety. The compounds of the invention, due at least in part to their high ionisation potential at physiological pH, have the unique properties of selectively for peripheral 5HT4 receptors over those of the CNS, good binding affinity, and selectively of 5HT4 receptors over other serotonin receptors.
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Page/Page column 64
(2010/02/12)
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- Indolylalkylidenehydrazine-carboximidamide derivatives as 5-hydroxytryptamine-6 ligands
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The present invention provides a compound of formula I and the use thereof for the therapeutic treatment of a disorder relating to or affected by the 5-HT6 receptor.
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Page/Page column 18
(2010/02/05)
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- Applications of parallel synthesis to lead optimization
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Parallel synthesis of focused compound libraries for hit confirmation and lead optimization are certainly important drivers for shortening the lead discovery phase in the pharmaceutical and crop protection industries. In this article we show with permission of Roche and Syngenta three real case studies where Polyphor synthesized focused libraries for lead validation and optimization using high-throughput parallel synthesis and purification techniques. The three examples differ significantly in the synthetic strategies which were employed as well as in the chemical complexity of the final products. A multigeneration approach towards insecticidal triazines, the application of a sequential three-component reaction towards insecticidal and fungicidal thiazoles and finally a multistep synthesis approach of advanced building blocks followed by a two-step final derivatization towards novel antiviral N-hydroxy-indolin-2-ones are presented. In all cases 100-200 analogues were synthesized using parallel synthesis in solution followed by purification of the final products by parallel flash or high-throughput (unattended) HPLC (coupled to MS) within four months. Promising biological results were obtained in all three cases.
- Altorfer, Michael,Ermert, Philipp,Faessler, Juerg,Farooq, Saleem,Hillesheim, Elke,Jeanguenat, Andre,Klumpp, Klaus,Maienfisch, Peter,Martin, Joseph A.,Merrett, John H.,Parkes, Kevin E.B.,Obrecht, Jean-Pierre,Pitterna, Thomas,Obrecht, Daniel
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p. 262 - 269
(2007/10/03)
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- Synthesis and antimycobacterial activity of new S-alkylisothiosemicarbazone derivatives
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A new series of S-alkylisothiosemicarbazones of 3- and 4-pyridincarboxaldehyde and 4-fluoro- and 4-trifluoromethylbenzaldehyde was synthesized and evaluated for biological activity against various Mycobacterium strains. Inhibitory activity against Mycobacterium tuberculosis H37Rv ATCC 27294 and INH-R ATCC 35822 was compared with activity against clinical isolated Mycobacteria as well as against MOTT. Some of newly prepared compounds showed best inhibitory values against clinical isolated Mycobacteria, besides to low citotoxicity values.
- Cocco, Maria Teresa,Congiu, Cenzo,Onnis, Valentina,Pellerano, Maria Luisa,Logu, Alessandro De
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p. 501 - 506
(2007/10/03)
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- The serotonin 5-HT4 receptor. 2. Structure-activity studies of the indole carbazimidamide class of agonists.
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A number of substituted indole carbazimidamides were prepared and evaluated as 5-HT4 receptor agonists by using the isolated field-stimulated guinea pig ileum preparation. Their selectivity for the 5-HT4 receptor was established by examining their affinity for other 5-HT receptors using radioligand-binding techniques. Several selective and highly potent full as well as partial agonists emerged from this study. For example, 1b,d were found to be the most potent, full 5-HT4 receptor agonist described so far (EC50 = 0.5 and 0.8 nM, respectively), being 6 and 4 times more potent than serotonin itself. On the other hand, 5b and 1h appeared as partial 5-HT4 receptor agonists in the nonstimulated guinea pig ileum preparation with potencies, evaluated against serotonin action, respectively similar (5b, Ki = 12 nM) to and 300-fold higher (1h, Ki = 0.04 nM) than serotonin.
- Buchheit,Gamse,Giger,Hoyer,Klein,Kloeppner,Pfannkuche,Mattes
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p. 2331 - 2338
(2007/10/02)
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- Synthesis of 3,4,5-Triamino-4H-1,2,4-triazole (Guanazine) and its 4-Arylideneamino Derivatives
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Synthetic methods for the preparation of 3,4,5-triamino-4H-1,2,4-triazole (guanazine) and its 4-arylideneamino derivatives are described.Guanazine, which can be used as an appropriate starting material in the syntheses of different bicyclic heterocycles, was readily obtained from thiosemicarbazide by treatment with mercuric oxide.Guanazine was also obtained from the S-methylisothio ether of thiosemicarbazide via a pyrolytic reaction.The 4-arylideneamino derivatives were either prepared by treatment of guanazine with an appropriate aromatic aldehyde, or by methods in which 1-arylidene-5-thiocarbamoyldiaminoguanidines are used as starting materials.
- Emilsson, Hakan
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p. 1077 - 1081
(2007/10/02)
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- Cyclization of Isothiosemicarbazones. 6. The Formation and Structures of N-Alkenyl-1,2,4-triazoles and Related Compounds
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Alkanophenone 4-alkenes in acetic acid in moderate to good yields with elimination of diethyl malonate and ethyl cyanoacetate, respectively.When geometrical isomerism is possible, the triazolylalkenes have the E configuration.Aldehyde 4--or 4--3-methylisothiosemicarbazones undergo cleavage in acid to alkyl- or arylmethanol O-acylates and the corresponding malonate or cyanoacetate ester.The yields of O-acylate range from good in aromatic to poor in aliphatic compounds.The proposed machanism for this acid-catalyzed cleavage of 4-(substituted vinyl)-3-methylisothiosemicarbazones involves a resonance-stabilized iminium cation as a common intermediate.
- Yamazaki, Chiji,Takada, Seiko,Suzuki, Kenji,Ishigami, Misaki
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p. 5513 - 5516
(2007/10/02)
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