scholarly journals A one-pot synthesis of 7,11-diaryl-2,4-diazaspiro[5,5]undecane-3-oxo (or thioxo)-1,5,9-triones

1970 ◽  
Vol 24 (2) ◽  
pp. 135-142
Author(s):  
M Giasuddin Ahmed ◽  
Syeda Asghari Ahmed ◽  
UKR Romman ◽  
Kawsari Akhter ◽  
Md Ershad Halim ◽  
...  

Spiro compounds 7,11-diaryl-2,4-diazaspiro[5,5]undecane-1,3,5,9-tetraones 3a-d were prepared by carrying out reactions between diarylideneacetones, (ArCH=CH)2C=O, 2a-d [Ar= 2-CH3C6H4, 4-CH3C6H4, 4-(CH3)2NC6H4 and 4-HOC6H4 respectively] and  barbituric acid (1a) under refluxing condition in aqueous ethanol medium without using any catalyst. Under similar conditions the corresponding 7,11-diaryl-3-thioxo-2,4-diazaspiro[5,5]undecane-1,5,9-triones 3e-g were synthesized from the reactions of diarylideneacetones 2a, 2d and 2e [Ar= 4-ClC6H4] with 2-thiobarbituric acid (1b). The structures of the spiro compounds were established with the help of their UV, IR, 1H NMR, 13C NMR and mass spectral data and elemental analyses. DOI: http://dx.doi.org/10.3329/jbcs.v24i2.9702 Journal of Bangladesh Chemical Society, Vol. 24(2), 135-142, 2011

2013 ◽  
Vol 25 (2) ◽  
pp. 124-131
Author(s):  
Mohammad Shahid Ullah ◽  
M Giasuddin Ahmed ◽  
UKR Romman ◽  
Kawsari Akhter ◽  
S Mosaddeq Ahmed ◽  
...  

Some 5, 7-diaryl-1,5-dihydro (or 1, 2, 3, 5-tetrahydro)- pyrano[2, 3-d] pyrimidin-2, 4- diones (or 2-thioxo-4-ones) (3a-g) has been synthesized in one-step by the cyclocondensation of barbituric acid or thiobarbituric acid (1) with arylideneacetophenones (2a-d), in glacial acetic acid in the presence of phosphorous pentoxide. The structures of the compounds 3a-g were determined by their UV, IR, 1H NMR, 13C NMR, mass spectral data and elemental analyses. Journal of Bangladesh Chemical Society, Vol. 25(2), 124-131, 2012 DOI: http://dx.doi.org/10.3329/jbcs.v25i2.15064


2013 ◽  
Vol 61 (2) ◽  
pp. 167-171 ◽  
Author(s):  
M Mahbubur Rahman ◽  
S Mosaddeq Ahmed ◽  
SMA Hakim Siddiki ◽  
Md Ershad Halim ◽  
Kawsari Akhter ◽  
...  

A number of 5, 7-diaryl-1,5-dihydro (or 1, 2, 3, 5-tetrahydro)- pyrano[2, 3-d] pyrimidin-2, 4-diones (or 2-thioxo-4-ones) (3a-f) have been synthesized in one-step by cyclocondensation of barbituric acid or thiobarbituric acid (1) with arylideneacetophenones (2a-c), in glacial acetic acid in the presence of phosphorous pentoxide. The structures of the compounds 3a-f have been determined by UV, IR, 1H NMR, 13C NMR, mass spectral data and elemental analyses. DOI: http://dx.doi.org/10.3329/dujs.v61i2.17065 Dhaka Univ. J. Sci. 61(2): 167-171, 2013 (July)


2013 ◽  
Vol 48 (1) ◽  
pp. 7-12
Author(s):  
MM Rahman ◽  
ME Halim ◽  
SM Ahmed ◽  
K Akhter ◽  
UKR Romman

Five oxime derivatives 7, 11-bis-(4-chlorophenyl)-3-thioxo-2,4-diazaspiro[5,5]undecane-1,5,9-trione-9-oxime (2a), 7,11-bis-(4- methoxyphenyl)-2,4-diazaspiro[5,5]undecane-1,3,5,9-tetraone-9-oxime (2b), 7,11-diphenyl-2,4-diazaspiro[5,5]undecane-1,3,5,9-tetraone- 9-oxime (2c), 7,11-bis-(4-methoxyphenyl)-3-thioxo-2,4-diazaspiro[5,5]undecane-1,5,9-trione-9-oxime (2d), 7,11-diphenyl-3-thioxo-2,4- diazaspiro[5,5]undecane-1,5,9-trione-9-oxime (2e) were synthesized from the corresponding 7,11-diaryl-2,4-diazaspiro[5,5]undecane-3- oxo (or thioxo)-1,5,9-triones (1a-e) with hydroxylaminehydrogenchloride in presence of pyrimidine in absolute alcohol. The structures of the compounds 2a-e were confirmed by their UV, IR, 1H NMR, 13C NMR and mass spectral data and elemental analyses. DOI: http://dx.doi.org/10.3329/bjsir.v48i1.15383 Bangladesh J. Sci. Ind. Res. 48(1), 7-12, 2013


2017 ◽  
Vol 52 (2) ◽  
pp. 115-124
Author(s):  
K Akhter ◽  
ME Halim ◽  
SM Ahmed ◽  
PK Sarkar ◽  
F Akter ◽  
...  

A number of new 5, 7-diaryl-1,5-dihydro (or 1, 2, 3, 5-tetrahydro)- pyrano [2, 3-d] pyrimidin-2, 4-diones (or 2-thioxo-4-ones) (3a-g) have  been synthesized in one-step by cyclocondensation of barbituric acid or thiobarbituric acid (1) with arylideneacetophenones (2a-d), in glacial  acetic acid in the presence of phosphorous pentoxide. The structures of the compounds 3a-g have been determined by UV, IR, 1H NMR, 13C  NMR, mass spectral data and elemental analyses. The compounds 3a-g do not seem to be available in the literature.Bangladesh J. Sci. Ind. Res. 52(2), 115-124, 2017


2016 ◽  
Vol 51 (2) ◽  
pp. 129-138
Author(s):  
K Akhter ◽  
SM Ahmed ◽  
Md E Halim ◽  
MA Kader ◽  
K Jahan ◽  
...  

Some new 5, 7-diaryl-1,5-dihydro (or 1, 2, 3, 5-tetrahydro)- pyrano[2, 3-d] pyrimidin-2, 4-diones (or 2-thioxo-4-ones) (3a-h) have been synthesized in one-step by cyclocondensation of barbituric acid or thiobarbituric acid (1) with arylideneacetophenones (2a-d), in glacial acetic acid in the presence of phosphorous pentoxide. The structures of the compounds 3a-h have been determined by UV, IR, 1H NMR, 13C NMR, mass spectral data and elemental analyses. The compounds 3a-h do not seem to be available in the literatureBangladesh J. Sci. Ind. Res. 51(2), 129-138, 2016


2021 ◽  
Vol 6 (2) ◽  
pp. 111-115
Author(s):  
H.P. Parekh ◽  
M.H. Chauhan ◽  
N.L. Solanki ◽  
V.H. Shah

In present work, a series of novel [1,2,4]triazolo[1,5-a]quinoline derivatives (HP-101-110) have been synthesized using multi-component reaction at room temperature in the presence of ammonium chloride as mild, cost effective green catalyst along with water as eco-friendly green solvent. The synthesis of 1,2,4-triazolo[1,5-a]quinolines (HP-101-110) was achieved by two step process. In first step, diversified Hantzsch pyridine reaction of an appropriate aromatic aldehyde, malononitrile, dimedone and benz hydrazide using ethanol as a solvent gives N-(2-amino-3-cyano-7,7-dimethyl-5-oxo-4-phenyl-5,6,7,8- tetrahydro-quinolin-1(4H)-yl)-4-hydroxybenzamide derivatives. In the second step, synthesis of the final product 2-(4-hydroxyphenyl)-8,8-dimethyl-6-oxo-5-phenyl-6,7,8,9-tetrahydro[1,2,4]triazolo[1,5- a]-quinoline-4-carbonitriles was achieved by the intramolecular cyclization of step 1 product.The structure of all the synthesized compounds (HP101-110) has been elucidated by FT-IR, 1H & 13C NMR, mass spectral data and elemental analyses.


2012 ◽  
Vol 25 (1) ◽  
pp. 62-70 ◽  
Author(s):  
Md Anwarul Hoque ◽  
Md Arzu Miah ◽  
Md Nurul Abser ◽  
Abul K Azad ◽  
Kamrun N Khan ◽  
...  

Treatment of 2-Mercaptothiazoline, 2-Mercaptobenzimidazole, 2-Mercapto-1- methylimidazole with [M2(CO)10] (M = Re and Mn) at ambient temperature in presence of decarbonylating reagent Me3NO give the complexes [Mn2(?-?2-C3H4NS2)2(CO)6] (1), [Re2(?-?2-C3H4NS2)2(CO)6] (2), [Mn2(?-?2-C7H5SN2)2(CO)6] (3), [Re2(?-?2- C7H5SN2)2(CO)6] (4), [Re2(?-?2-C4H5N2S)2(CO)6] (5) and [Re2(?1-C4H5N2SH)(CO)9] (6) respectively. All the compounds have been characterized by IR, 1H NMR and mass spectral data. The heterocyclic ligands are expected to be coordinated to two or single metal atom through the nitrogen and sulfur atoms or via only sulfur atom.DOI: http://dx.doi.org/10.3329/jbcs.v25i1.11775 Journal of Bangladesh Chemical Society, Vol. 25(1), 62-70, 2012> 


2007 ◽  
Vol 54 (3) ◽  
pp. 561-565 ◽  
Author(s):  
A Selcen Alpan ◽  
H Semih Gunes ◽  
Zeki Topcu

Benzimidazole is one of the most important heterocyclic groups manifesting various biological properties, such as antibacterial, antifungal, antimicrobial, antiprotozoal and antihelmintic activities. Several benzimidazole derivatives are also active as inhibitors of type I DNA topoisomerases. In this study, three 1H-benzimidazole derivatives with different electronic characteristics at position 5-, namely 5-chloro-4-(1H-benzimidazole-2-yl)phenol (Cpd I), 5-methyl-4-(1H-benzimidazole-2-yl)phenol (Cpd II) and 4-(1H-benzimidazole-2-yl)phenol (Cpd III), were synthesized and evaluated for their effects on mammalian type I DNA topoisomerase activity using quantitative in vitro plasmid supercoil relaxation assays. For the structure elucidation of the compounds, melting points, UV, IR, 1H NMR, 13C NMR, mass spectral data and elemental analyses were interpreted. Among the compounds, 5-methyl-4-(1H-benzimidazole-2-yl)phenol (Cpd II) manifested relatively potent topoisomerase I inhibition.


Author(s):  
PRABHAKER WALMIK

Objective: The objective of the study was to synthesis of 1,2,3,4-tetrahydro-4-oxo-6-(5-substituted 2-phenyl-1H-indol-3-yl)-2-thioxopyrimidine-5- carbonitrile derivatives (4a-c). Methods: The structures of all these unknown compounds have been confirmed with the help of physical and spectral techniques such as IR, 1H, and 13C NMR and mass spectral data and these newly synthesized compounds were evaluated for in-vitro antimicrobial and antitubercular activities. Results: Screening studies have demonstrated that the newly synthesized compound 4a exhibited promising antimicrobial and antitubercular properties. Conclusion: The final results revealed that compound 4a exhibited promising antimicrobial and antitubercular properties when compared to the standard drugs.


2020 ◽  
Vol 32 (3) ◽  
pp. 683-689
Author(s):  
Blassan Samuel ◽  
Madhvesh Pathak

A new class of moisture stable heteroleptic titanium(IV) complexes, synthesized from 8-hydroxyquinoline of the type [(Q)2Ti(2-O-5-X-C6H3CH2NC6H4R] (3a-j), was prepared by reacting the antecedent molecule [(Q2)Ti(OiPr)2] (2) with various 2-hydroxy-N-phenyl-benzylamine analogues in 1:1 molar ratios in dry toluene (where, HQ = 8-hydroxyquinoline; iPr = isopropyl; R = H, 4-CH3, 4-OCH3, 2-Cl, 4-Cl, 2-Br, 4-Br; X= H, Br). Moisture sensitive study disclosed that these new metal complexes were unreacted for 72 h. Mass spectral data were employed for proving the mono-nuclearity of the new derivatives. Thermal decomposition pattern of the new derivatives was explained by thermogravimetric analyses. Elemental analyses data are in concordance with their expected values. The hexa-coordinated way of titanium-ligand linkage is further proved through NMR, FTIR, and UV-visible spectral studies. The cytotoxic efficiency of new complexes was tested against MDA-MB-231 human breast carcinoma cell line. Complex 3a exhibited the highest cytotoxic potential of 0.039 μM in comparison to all its analogues of this series by employing cisplatin as the standard


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