Synthesis and basicity of 2-<i>N</i>-quinolyl- and 2-<i>N</i>-isoquinolyl-1,1,3,3-tetramethylguanidines

Foroughifar, Naser; Leffek, Kenneth T.; Lee, Yong Gu

doi:10.1139/v93-023

Cited by 7 publications

(5 citation statements)

References 3 publications

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“…The compound 1,1,3,3-tetramethyl-2-(quinoline-8yl)guanidine (Figure 9), with a pK a value of 11.7 in water and 20.5 in CH 3 CN, was first synthesized by Foroughifar, Leffek, and Lee. 117 Later Herres-Pawlis et al optimized its yield and used the compound as ligand in coordination chemistry. 118 Basicity measurements for bis-and oligoguanidines are often hampered by the presence of several protonation steps.…”

Section: Account Syn Lettmentioning

confidence: 99%

Guanidines as Reagents in Proton-Coupled Electron-Transfer Reactions and Redox Catalysts

Himmel

2018

Synlett

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Redox-active guanidines are ideal proton-coupled electron-transfer (PCET) reagents, since they combine a high Brønsted basicity with a low and tunable redox potential. In this article, the development of redox-active guanidines (especially guanidino-functionalized aromatics, GFAs) in the last ten years is summarized, and their properties compared to other organic Brønsted bases and organic electron donors. First, some applications in organic chemistry that purely use the redox activity (formation of organic donor–acceptor materials and photochemical reductive C–C coupling reactions) are presented. Then, reactions that involve both proton and electron transfer are reviewed. In stoichiometric reactions, redox-active guanidines are used for the dehydrogenative coupling of thiols and phosphanes. The first redox catalytic applications are discussed, using dioxygen as green oxidizing reagent.1 Introduction2 Redox-Active Amines and Guanidines3 Brønsted Basicity of Amines and Guanidines4 Variations of GFA Compounds5 GFA Compounds in Organic Donor–Acceptor Materials and as Reducing Reagents in Organic Synthesis6 Stoichiometric Dehydrogenative Coupling Reactions with Redox-Active Guanidines7 Guanidines as Redox Catalysts8 Conclusions and Outlook

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Section: Account Syn Lettmentioning

confidence: 99%

Guanidines as Reagents in Proton-Coupled Electron-Transfer Reactions and Redox Catalysts

Himmel

2018

Synlett

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“…The corresponding ligand (L) prepared according to the previously published procedure (Foroughifar et al, 1993). To a solution of 1,1,3,3 tetramethyl urea (1 m mol) in 10 ml dry benzene was added drop-wise to a solution of POCl 3 (4 m mol) in 20 ml dry benzene.…”

Section: Procedures For Synthesis Ofmentioning

confidence: 99%

Synthesis, Characterization and Biological Activity of Novel Zirconium, Zinc and Cadmium Complexes Derived from Substituted Tetramethyl Guanidine

Pasdar

Foroughifar²,

Saghavaz³

et al. 2017

IJC

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A novel series of metal complexes of guanidine ligand derived from condensation of 1,1,3,3-tetramethylurea and 2-aminopyridine in present of POCl 3 have been synthesized. The complexes are characterized using FTIR, UV-Vis and also molar conductance was measured. These spectroscopic studies confirmed that the ligand bonded to the metals through the nitrogen atoms. The suggested structures of the metal complexes are square planner. The ligand and its metal complexes were tested against Gram-negative bacteria; Escherichia coli, Serratia marcescens and Gram-positive bacteria; Bacillus sabtilis and Staphylococcus aureus by applying disc diffusion method. The most antibacterial activity of synthesized compounds belongs to CdL 2 complex. The results of this study showed that the metal complexes have more antibacterial activity against species when compared to the parent ligand.

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“…In the case of 4a-f, C 2 -H of the 1,3,4-oxadiazole ring appeared as a singlet at the deshielding area δ = 6.87-7.12 ppm, while the methyl protons attached to C 2 of the 1,3,4-oxadiazole ring for 4 g-k appeared as a singlet at δ = 2.22-2.56 ppm. On the other hand, when benzaldehyde hydrazone derivatives (R = H) 3a-f were stirred for 2 days with concentrated sulfuric acid [45] at room temperature, they underwent cyclization reaction to give 2,3-dihydro-5-(2hydroxyphenyl)-2-aryl-1,3,4-oxadiazoles 5a-f (Scheme 1). It is noteworthy that treatment of acetophenone hydrazone derivatives (R = CH 3 ) 3 g-k with concentrated sulfuric acid and subsequent neutralization using 10% Na 2 CO 3 resulted in formation of the starting 2-hydroxybenzohydrazide 2 and acetophenone derivatives.…”

Section: Synthesis Of 1 3 4-oxadiazoles From Hydrazide Hydrazonesmentioning

confidence: 99%

Synthesis and Biological Evaluation of Some Heterocyclic Compounds from Salicylic Acid Hydrazide

Sarshira

Hamada

Moghazi

et al. 2015

Journal of Heterocyclic Chem

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Different heterocyclic compounds were prepared starting from 2‐hydroxy benzohydrazide; for example, cyclization of hydrazide hydrazone 3 derived from 2‐hydroxybenzohydrazide 2 with acetic anhydride or concentrated sulfuric acid gave 1,3,4‐oxadiazole derivatives 4–5. On the other hand, direct cyclization of 2‐hydroxy benzohydrazide 2 with one carbon cyclizing agent gave a new derivative of 1,3,4‐oxadiazole 7, 8, 9, 10, 11. Heating of hydrazide hydrazone 3 with thioglycolic acid in pyridine gave thiazolidinone 12. When 2‐hydroxy benzohydrazide 2 reacted with aliphatic carboxylic acids such as formic acid or acetic acid, it gave the corresponding N‐formyl or N‐acetyl derivatives 6. Subsequent cyclization of 6 using phosphorous pentasulphide in pyridine gave 1,3,4‐thiadiazoles 13. Cyclization of 2‐hydroxy benzohydrazide with ethyl acetoacetate gives pyrazolone derivative 14. Finally, when an ethanolic solution of acid hydrazide 2 was treated with ammonium thiocyanate in 35% HCl, it gave the thiosemicarbazide 15. Subsequent treatment of 15 with concentrated sulfuric acid or 10% sodium hydroxide gave 5‐amino‐1,3,4‐thiadiazole 16 and 1,2,4‐triazole 17, respectively. The structures of all newly isolated compounds were confirmed using 1H NMR, IR spectra, and elemental analyses. The antimicrobial activities for all isolated compounds were examined against different microorganisms.

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Synthesis and basicity of 2-N-quinolyl- and 2-N-isoquinolyl-1,1,3,3-tetramethylguanidines

Cited by 7 publications

References 3 publications

Guanidines as Reagents in Proton-Coupled Electron-Transfer Reactions and Redox Catalysts

Guanidines as Reagents in Proton-Coupled Electron-Transfer Reactions and Redox Catalysts

Synthesis, Characterization and Biological Activity of Novel Zirconium, Zinc and Cadmium Complexes Derived from Substituted Tetramethyl Guanidine

Synthesis and Biological Evaluation of Some Heterocyclic Compounds from Salicylic Acid Hydrazide

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