Approaches to the Synthesis of 5-Benzylidene-2-imidazolin-4-ones

1990 ◽  
Vol 43 (2) ◽  
pp. 367 ◽  
Author(s):  
RH Prager ◽  
C Tsopelas
Keyword(s):  
Acetic Anhydride ◽  
Aromatic Aldehydes ◽  
Darzens Reaction ◽  
Derivatives Of

Aromatic aldehydes , but not ketones, can be condensed with glycocyamidine . The corresponding alkylbenzylideneglycocyamidines may be made from glycidic esters by reaction with guanidine, followed by cyclization with acetic anhydride. A number of mono- and di -acetylated derivatives of 6,7-dihydropyrrolo[2,3-c]azepine-4,8(1H,5H)- dione have been prepared, but failed to undergo the Darzens reaction. Bromo- and iodo-2-arylazoimidazoles, protected on nitrogen by the methoxyethoxymethyl group, failed to undergo clean lithiation.

Syntheses and Cytotoxicity Screening of some Novel 1,2,4-Triazine Derivatives against Liver Carcinoma Cell Lines

2020 ◽  
Vol 17 ◽  
Author(s):  
W. Abd El-Fattah
Keyword(s):  
Acetic Anhydride ◽  
Cell Lines ◽  
Carcinoma Cell ◽  
Aromatic Aldehydes ◽  
Liver Carcinoma ◽  
Anticancer Activities ◽  
Carcinoma Cell Lines ◽  
Elemental Analyses ◽  
Triazine Derivatives ◽  
C Nmr

: In this work, 1,2,4-triazine derivatives were synthesized and evaluated for anticancer activities. Series of 1,2,4-triazine derivatives (4a, b) were prepared via the reaction of N-benzoyl glycine (1) with aromatic aldehydes in presence of fused sodium acetate and acetic anhydride to give 1,3-oxazolinone derivatives (2a, b), followed by condensation with 1-(ethoxycarbonyl) hydrazine (3) in glacial acetic acid. Compounds (4a, b) then reacted with acetic anhydride, ethyl chloroacetate and 2,4-dinitrophenyl hydrazine yielded the corresponding to N-acetyl derivatives (5a, b), N-(ethoxycarbonyl) methyl derivative (6) and 1,2-disubstituted hydrazine (7), respectively. The structures of the 1,2,4-triazine derivatives were confirmed by IR, 1H, 13C NMR, MS and elemental analyses. Anticancer activity of some 1,2,4-triazine derivatives (4-7) have been investigated. The results revealed that compounds 4a (IC50= 2.7μM), 5a (IC50= 1.5μM), and 5b (IC50= 3.9μM) show promising inhibitory growth efficacy compared to a standard antitumor drug (IC50= 4.6μM). These three compounds can be considered as potential agents against human hepatocellular carcinoma cell lines (HepG-2).

scholarly journals Synthesis and biological activity of 4-thiazolidinone derivatives of phenothiazine

2012 ◽  
Vol 77 (1) ◽  
pp. 17-26 ◽  
Author(s):  
Ritu Sharma ◽  
Pushkal Samadhiya ◽  
Savitri Srivastava ◽  
Santosh Srivastava
Keyword(s):  
Antimicrobial Activity ◽  
Heterocyclic Compounds ◽  
Thioglycolic Acid ◽  
Cycloaddition Reaction ◽  
Aromatic Aldehydes ◽  
Knoevenagel Reaction ◽  
Antituberculosis Activity ◽  
Bacteria And Fungi ◽  
Derivatives Of ◽  
Anhydrous Zncl2

A new series of N-[3-(10H-phenothiazinyl)-propyl]-2-(substituted phenyl)-4-oxo-5-( substituted benzylidene)-1,3-thiazolidine-carboxamide, 5(as) have been synthesized. The cycloaddition reaction of thioglycolic acid with N-[3-(10H-phenothiazinyl)-propyl]-N?-[(substituted phenyl)-methylidene]- urea, 3(a-s) in the presence of anhydrous ZnCl2 afforded new heterocyclic compounds N-[3-(10H-phenothiazinyl)-propyl]-2-(substituted phenyl)-4-oxo- 1,3-thiazolidine-carboxamide, 4(a-s). The later product on treatment with several selected substituted aromatic aldehydes in the presence of C2H5ONa undergoes Knoevenagel reaction to yield 5(a-s). The structure of compounds 1, 2, 3(a-s), 4(a-s) and 5(a-s) were confirmed by IR, 1H NMR, 13C NMR, Fmass and chemical analysis. All above compounds were screened for their antimicrobial activity against some selected bacteria and fungi and for antituberculosis activity compounds have been screened against the bacterium M. tuberculosis.

scholarly journals SYNTHESIS AND PRELIMINARY PHARMACOLOGICAL EVALUATION OF NEW NAPROXEN ANALOGUES HAVING 1, 2, 4-TRIAZOLE-3-THIOL

2017 ◽  
Vol 9 (7) ◽  
pp. 66
Author(s):  
Monther F. Mahdi ◽  
Noor H. Naser ◽  
Nethal H. Hammud
Keyword(s):  
Aromatic Aldehydes ◽  
Heterocyclic Ring ◽  
Inflammatory Activity ◽  
Control Group ◽  
Paw Edema ◽  
Dose Equivalent ◽  
Edema Model ◽  
Anti Inflammatory ◽  
Derivatives Of

Objective: The objective of this search was to synthesize a new naproxen analogues having a 1,2,4-triazole-3-thiol heterocyclic ring, and preliminary pharmacological assessment of the anti-inflammatory activity of the synthesized compounds. Methods: The synthesis of naproxen analogues that having 1,2,4-triazole-3-thiol heterocyclic ring occur through esterification of naproxen, and then its reaction with hydrazine hydrate, and carbon disulfide, finally different aromatic aldehydes reacted with triazole derivatives of naproxen containing amino group to produce schiff bases.Results: In vivo acute anti-inflammatory activity of the synthesize compounds (Va-Vd) was evaluated in rats using egg-white induced edema model of inflammation in a dose equivalent to (50 mg/kg) of naproxen. All tested compounds were produced a significant reduction in paw edema with respect to the effect of propylene glycol 50% v/v (control group). Compound Vd produced superior anti-inflammatory activity compared to naproxen.Conclusion: The results obtained in this work give evidence about the valid synthesis of 1,2,4 triazole-3-thiol derivatives of naproxen, which reacted with different aldehydes to yield several schiff bases. The incorporation of benzaldehyde possess para-electron donating group (para-hydroxyl benzaldehyde) will increase the anti-inflammatory activity of naproxen.

ChemInform Abstract: NITRO DERIVATIVES OF THE THIOPHENE SERIES. 4. NITRATION OF THIOPHENE DERIVATIVES BY METAL NITRATES IN ACETIC ANHYDRIDE

1981 ◽  
Vol 12 (50) ◽  
Author(s):  
YU. D. CHURKIN ◽  
L. V. PANFILOVA ◽  
V. D. LUGOVOI ◽  
N. V. BOIKAO
Keyword(s):  
Acetic Anhydride ◽  
Thiophene Series ◽  
Metal Nitrates ◽  
Nitro Derivatives ◽  
Thiophene Derivatives ◽  
Derivatives Of

CXIV.—Action of aromatic aldehydes of derivatives of β-naphthylamine

1900 ◽  
Vol 77 (0) ◽  
pp. 1210-1219
Author(s):  
Gilbert Thomas Morgan
Keyword(s):  
Aromatic Aldehydes ◽  
Derivatives Of

Efficient Second Harmonic Generation in Hydrazone, Derivatives of Substituted Aromatic Aldehydes

1989 ◽  
Vol 173 ◽  
Author(s):  
Richard S. Potember ◽  
Robert C. Hoffman ◽  
Karen A. Stetyick
Keyword(s):  
Second Harmonic Generation ◽  
Harmonic Generation ◽  
Second Harmonic ◽  
Harmonic Signal ◽  
Aromatic Aldehydes ◽  
Dihydrogen Phosphate ◽  
Ammonium Dihydrogen Phosphate ◽  
Harmonic Signals ◽  
Derivatives Of ◽  
Second Harmonic Signal

ABSTRACTHydrazone, 1,1-dimethylhydrazone, methylhydrazone, phenylhydrazone and p-nitrophenyl hydrazone derivatives of substituted aromatic aldehydes were prepared and screened for second harmonic generation using the Kurtz powder technique. One compound, 4-nitro-3-methoxybenzaldehyde hydrazone exhibited a second harmonic signal up to 32 times that of ammonium dihydrogen phosphate (ADP) and 4-nitrobenzaldehyde hydrazone exhibited a second harmonic signal five times higher than previously reported, up to 40 times that of ADP. 3-methyl-4-nitrobenzaldehyde hydrazone, 4-nitrobenzaldehyde phenylhydrazone, 1-naphthaldehyde phenylhydrazone, 1-pyrenecarboxaldehyde phenylhydrazone exhibited second harmonic signals 25, 2.5, 5 and 20 times that of an ADP standard.

scholarly journals The first in situ synthesis of 1,3-dioxan-5-one derivatives and their direct use in Claisen-Schmidt reactions

2019 ◽  
Vol 25 (1) ◽  
pp. 85-90 ◽  
Author(s):  
M. Javad Poursharifi ◽  
Mohammad M. Mojtahedi ◽  
M. Saeed Abaee ◽  
Mohammad M. Hashemi
Keyword(s):  
Acetic Acid ◽  
Aromatic Aldehydes ◽  
In Situ Synthesis ◽  
Stepwise Procedures ◽  
Time Periods ◽  
High Yields ◽  
Short Time ◽  
Direct Use ◽  
Derivatives Of

AbstractA method is developed for in situ generation of 1,3-dioxan-5-one derivatives 2. These compounds are simple precursors for accessing carbohydrate structures and previously had to be produced via stepwise procedures using excessive amounts of reagents. In the present work, three different derivatives of 2 were synthesized via the reaction of trialkoxyalkanes with dihydroxyacetone dimer 1 in the presence of acetic acid as the catalyst. In the same pot, derivatives of 2 were reacted with aromatic aldehydes and 30 mol% of pyrrolidine to obtain high yields of the respective bischalcones 3 within short time periods.

ChemInform Abstract: ON REACTIONS OF 6-METHOXY-1,2,3,4-TETRAHYDRO-BETA-CARBOLINONES-(1) AND THEIR DICHLOROPHOSPHORYLS WITH ACETIC ANHYDRIDE, SYNTHESIS OF 5-ACETYL DERIVATIVES OF THE BETA-CARBOLINE SERIES

1975 ◽  
Vol 6 (51) ◽  
pp. no-no
Author(s):  
L. N. YAKHONTOV ◽  
M. YA. URITSKAYA ◽  
O. S. ANISIMOVA ◽  
T. YA. FILIPENKO ◽  
K. F. TURCHIN ◽  
...  
Keyword(s):  
Acetic Anhydride ◽  
Derivatives Of

ChemInform Abstract: BISINDOLES. 15. ACID CONDENSATION OF 2,2′-ETHOXYCARBONYL DERIVATIVES OF BIS(5-INDOLYL) OXIDE AND BIS(5-INDOLYL)METHANE WITH AROMATIC ALDEHYDES

1983 ◽  
Vol 14 (32) ◽  
Author(s):  
D. M. TABIDZE ◽  
N. A. KOGAN ◽  
I. SH. CHIKVAIDZE ◽  
SH. A. SAMSONIYA ◽  
N. N. SUVOROV
Keyword(s):  
Aromatic Aldehydes ◽  
Derivatives Of

Notizen: The Synthesis of a New Fused Thiazolo [4,3-c] -1,2,4-triazole System and its Derivatives

1976 ◽  
Vol 31 (6) ◽  
pp. 853-856 ◽  
Author(s):  
Nazmi Abd Elatif Kassab ◽  
Sanaa Osman Abd Allah ◽  
Hamed Abdel Reheem Ead
Keyword(s):  
Potassium Salt ◽  
Aromatic Aldehydes ◽  
Alkyl Halides ◽  
Formaldehyde Solution ◽  
Derivatives Of

Cyclisation of the 4-phenylhydrazono derivatives of 2-thiazolidinone or 2-thiazolidinethione (1) with formaldehyde solution or with aromatic aldehydes yields 2-phenyl-2,3-dihydrothiazolo[4,3-c]-1,2,4-triazol-5-one or its 5-thiocarbonyl analogue (2). Condensing 2 with aromatic aldehydes afforded the corresponding 7-arylidene derivatives (8).The 5-arylidene derivatives of 4-anisylimino-2-thiazolidinethione (5) were obtained by condensing 4 with aromatic aldehydes. The potassium salt of 5 reacts readily with alkyl halides to yield the 5-arylidene derivatives of 4-anisylimino-2-alkylmercapto-2-thiazoline (6).

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