A Convenient Synthesis of Some Pyrazolinone and Pyrazole Derivatives

Aly, El-Saied A.; Abdo, M.A.; El‐Gharably, Atif A.

doi:10.1002/jccs.200400146

Cited by 14 publications

(6 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For compounds 15 and 16 bearing ortho-and para-Cl phenyl substituents, respectively, at the N-1 position, the induction effect of the N-1 para-Cl substituent was stronger than ortho-Cl (77% vs. 72%, Table 2). All 6-[(formyloxy)methyl]-1H-pyrazolo [3,4-d]pyrimidines (17)(18)(19)(20)(21)(22)(23)(24)(25)(26)(27)(28)(29)(30) were characterized by spectroscopic methods. The structure of 6-[(formyloxy)methyl]-1H-pyrazolo [3,4-d]pyrimidine 24 was also characterized by X-ray crystallography and the ORTEP drawing is shown in Fig.…”

Section: Resultsmentioning

confidence: 99%

“…Pyrazolopyrimidines can also be accessed via heterocyclization using starting materials such as 5-amino-4formypyrazoles, 22 5-amino-1H-4-pyrazolcarbonitriles, 23 and 5amino-1H-4-pyrazolcarboxamides. [23][24][25][26] However, the method for preparing pyrazolopyrimidines involves harsh conditions, long reaction times, complex synthetic procedures, and tedious purication steps. 27 Therefore, convenient synthetic routes for the synthesis of pyrimidine fused heterocyclic systems have attracted considerable attention.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Vilsmeier reagent-mediated synthesis of 6-[(formyloxy)methyl]-pyrazolopyrimidines via a one-pot multiple tandem reaction

Liu

Wong

2015

RSC Adv.

View full text Add to dashboard Cite

A new Vilsmeier reagent mediated one-pot reaction using 5-(2-chloroacetylamino)pyrazoles as the starting material was developed for the efficient synthesis of 6-[(formyloxy)methyl]-1H-pyrazolo[3,4-d]pyrimidine. This new multiple tandem reactions involving Vilsmeier-Haack reaction, Morgan-Walls reaction, sequential elimination, substitution reaction, and final hydrolysis reaction efficiently afforded formyloxymethyl pyrazolo[3,4-d]pyrimidine products in good yields.Morgan-Walls cyclization reaction, sequential elimination, substitution reaction, and hydrolysis for synthesis of the pyrazole fused pyrimidine derivatives via a tandem multiple reaction. 14,16Pyrimidines fused with a heterocycle such as furo-, 17 pyrazolo-, 18 pyrrolo-, 19 pyridopyrazolo-, 20 and pyrazolotriazolo-pyrimidine 21 are important classes of compounds and also currently of interest to the pharmaceutical industry due to their

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Vilsmeier reagent-mediated synthesis of 6-[(formyloxy)methyl]-pyrazolopyrimidines via a one-pot multiple tandem reaction

Liu

Wong

2015

RSC Adv.

View full text Add to dashboard Cite

show abstract

“…The initial precursors (2-4) were prepared with reported protocols and compared with the literature data. [45][46][47][48] General Procedure for the synthesis of bispyrazolyl-1,3,4oxadiazoles 5 (a-f)…”

Section: Methodsmentioning

confidence: 99%

Synthesis, in vitro α‐Glucosidase Inhibition, DFT Calculations, and Molecular Docking Studies of Some New Substituted 2,5‐Bis(pyrazolyl)‐1,3,4‐oxadiazoles

Chaudhry,

Abdullah,

un‐Nisa

et al. 2024

ChemistrySelect

View full text Add to dashboard Cite

A pivotal feature of present research study is the synthesis of some new 2,5‐bis(pyrazolyl)‐1,3,4‐oxadiazoles as promising α‐glucosidase inhibitors. In this regard, a facile reaction scheme was designed to afford 1,3,4‐oxadiazole ring. In search of the most favourable reaction condition, a model reaction was first carried out between 1,3‐diphenyl‐1H‐pyrazole‐4‐carbohydrazide (3) and 1,3‐diphenyl‐1H‐pyrazole‐4‐carboxylic acid (4 a) using phosphorous oxychloride (POCl3). The results emanated from this model reaction were utilized to prepare other derivatives to highlight the scope of current synthetic approach and the structures of the prepared molecules were characterized from spectroscopic techniques. These derivatives were further investigated for their α‐glucosidase inhibitory potentials. 2,5‐Bis(1,3‐diphenyl‐1H‐pyrazol‐4‐yl)‐1,3,4‐oxadiazole (5 a) and 2‐(3‐(4‐bromophenyl)‐1‐phenyl‐1H‐pyrazol‐4‐yl)‐5‐(1,3‐diphenyl‐1H‐pyrazol‐4‐yl)‐1,3,4‐oxadiazole (5 c) displayed strong in vitro inhibitory activities with IC50 73.1±1.13 μM and IC50 87.3±1.12 μM respectively with least toxicity profiles. Molecular docking and computational studies including geometry optimization of synthesized molecular systems, calculations of their orbital energies, and molecular electrostatic potential (MEP) surface maps further helped to establish structural and electronic properties contributing towards their bioactivity. The electrophilicity index significantly quantifies the biological activity. The experimental and computational data altogether facilitated in understanding the therapeutic attributes of these versatile scaffolds in relation to their α‐glucosidase inhibition.

show abstract

“…Synthesis of pyrrolo [2,3-c]pyrazole derivatives 3a and 3b. 55 reported that treatment of 5-azido-1-phenyl-3-pyridin-4-yl-1H-pyrazole-4-carbaldehyde 6 with hydrazine hydrate 7 in the presence of acetic acid in ethanol at reflux yielded 1-phenyl-3-pyridin-4-yl-1,6-dihydropyrazolo [3,4-c]pyrazole 8. On the other hand, treatment of 7 with hydrazine hydrate 7 at room temperature in the presence of iodine afforded 6-phenyl-4-pyridin-4-yl-6H-pyrazolo [3,4-c]pyrazol-2-ylamine 9 (Scheme 3).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of various pyrazole-fused heterocyclic systems using pyrazole-4-carbaldehydes as versatile precursors

Abdelhamid¹,

Hawass²,

Sanad³

et al. 2021

Arkivoc

View full text Add to dashboard Cite

The discovery of intriguing properties shown by a large number of pyrazole derivatives has sparked a surge in interest in pyrazole chemistry over the last decade. They exist in a variety of natural products, dyes, and as scaffolds in a variety of drugs and pharmaceutical active ingredients. This review demonstrated various methods for the construction of pyrazole-fused heterocycles using pyrazole-4-carbaldehydes as effective precursors. Heterocyclic compounds mentioned in this review are arranged into categories based on the size of the heterocyclic ring as well as the position and number of the heteroatoms..

show abstract

A Convenient Synthesis of Some Pyrazolinone and Pyrazole Derivatives

Cited by 14 publications

References 9 publications

Vilsmeier reagent-mediated synthesis of 6-[(formyloxy)methyl]-pyrazolopyrimidines via a one-pot multiple tandem reaction

Vilsmeier reagent-mediated synthesis of 6-[(formyloxy)methyl]-pyrazolopyrimidines via a one-pot multiple tandem reaction

Synthesis, in vitro α‐Glucosidase Inhibition, DFT Calculations, and Molecular Docking Studies of Some New Substituted 2,5‐Bis(pyrazolyl)‐1,3,4‐oxadiazoles

Synthesis of various pyrazole-fused heterocyclic systems using pyrazole-4-carbaldehydes as versatile precursors

Contact Info

Product

Resources

About