scispace - formally typeset
Search or ask a question
Journal ArticleDOI

Catalyst-free, one-pot, three-component synthesis of 5-amino-1,3-aryl-1 $$H$$ -pyrazole-4-carbonitriles in green media

27 Apr 2013-Molecular Diversity (Springer Netherlands)-Vol. 17, Iss: 3, pp 459-469
TL;DR: An efficient, one-pot, three-component synthesis of various biologically important heterocyclic compounds is described via a tandem Knoevengel-cyclo condensation reaction of aromatic aldehydes, malono derivatives, and phenyl hydrazine derivatives in water and ethanol at room temperature.
Abstract: An efficient, one-pot, three-component synthesis of various biologically important heterocyclic compounds is described via a tandem Knoevengel-cyclo condensation reaction of aromatic aldehydes, malono derivatives, and phenyl hydrazine derivatives in water and ethanol at room temperature.
Citations
More filters
Journal ArticleDOI
TL;DR: In this article, six pyrazole and pyrazolone derivatives were synthesized and evaluated as corrosion inhibitors for copper alloy dissolution in basic medium using weight loss, polarization and electrochemical impedance measurements.

74 citations

Journal ArticleDOI
TL;DR: This systematic review covers the published studies from 1990 to date and provides an overview on the recent advances in synthetic approaches for the preparation of pyrazoles, including eco-friendly methodologies, heterogeneous catalytic systems, ligand-free systems, ultrasound and microwave-assisted reactions.
Abstract: Pyrazole, a five-membered heterocycle containing two nitrogen atoms, is extensively found as a core framework in a huge library of heterocyclic compounds that envelops promising agro-chemical, fluorescent and biological potencies. Attributed to its several potential applications, there is a rise in the significance of designing novel pyrazoles, disclosing innovative routes for synthesizing pyrazoles, examining different potencies of pyrazoles, and seeking for potential applications of pyrazoles. This review consists of two parts. The first part provides an overview on the recent developments in synthetic approaches to pyrazoles, which is related to the new or advanced catalysts and other ‘environment-friendly’ procedures, including heterogeneous catalytic systems, ligand-free systems, ultrasound and microwave-assisted reactions. The second part focuses on the recently reported novel biological affinities of pyrazoles. This systematic review covers the published studies from 1990 to date. It is expected that this review will be helpful in future research and for new thoughts in the quest for rational designs for developing more promising pyrazoles. The review consists of two parts: (i) an overview on the recent advances in synthetic approaches for the preparation of pyrazoles, including eco-friendly methodologies, heterogeneous catalytic systems, ligand-free systems, ultrasound and microwave-assisted reactions, and (ii) a summary of recently reported novel biological affinities of pyrazoles.

72 citations


Cites background from "Catalyst-free, one-pot, three-compo..."

  • ...to give pyridazine derivatives that are found to be good intermediates for the formation of fused heterocycles.(55) The reaction of MND with diazonium chloride salts of aniline derivatives yields intermediate substituted arylhydrazones 110a–b, that readily cyclizes in basic medium providing pyridazinimine derivatives 111a–b (Scheme 29)....

    [...]

Journal ArticleDOI
TL;DR: In this article, an efficient one pot multi-component sequential reaction of phenyl hydrazine, malanonitrile and a diverse range of aldehydes to afford highly functionalised pyrazoles is reported.
Abstract: An efficient one pot multi-component sequential reaction of phenyl hydrazine, malanonitrile and a diverse range of aldehydes to afford highly functionalised pyrazoles is reported. The reaction proceeds in water using molecular iodine as a catalyst, with no by-product formation, and involves simple operation requiring no column chromatography. Thus, this protocol fulfils all of the criteria that define green chemistry.

47 citations

Journal ArticleDOI
TL;DR: In this paper, a grinding-induced synthesis of highly functionalised pyrazoles derivatives by use of malanonitrile, phenyl hydrazine and diversified aldehyde is described.
Abstract: Grinding induced synthesis of highly functionalised pyrazoles derivatives by use of malanonitrile, phenyl hydrazine and diversified aldehyde. Ionic liquid is used as a catalyst with water, and no by-products form. A high yield is obtained and simple handling are the benefits of the adopted route, and this route fulfils all shades of green chemistry.

41 citations

References
More filters
Book
30 Sep 1997
TL;DR: In this article, the CHEC III is organized in 15 volumes and closely follows the organization used in the previous edition: Volumes 1 and 2: Cover respectively three and four-membered heterocycles, together with all fused systems containing a three- or four-measured heterocyclic ring.
Abstract: CHEC III is organized in 15 Volumes and closely follows the organization used in the previous edition: Volumes 1 and 2: Cover respectively three- and four-membered heterocycles, together with all fused systems containing a three- or four-membered heterocyclic ring. Volume 3: Five-membered rings with one heteroatom together with their benzo- and other carbocyclic-fused derivatives. Volumes 4, 5 and 6: Cover five-membered rings with two heteroatoms, and three or more heteroatoms, respectively, each with their fused carbocyclic compounds. Volumes 7, 8 and 9: Dedicated to six-membered rings with one, two, and more than two heteroatoms, respectively, again with the corresponding fused carbocylic compounds. Volumes 10, 11 and 12: Cover systems containing at least two directly fused heterocyclic five- and/or six-membered rings: of these Volume 10 deals with bi-heterocyclic rings without a ring junction heteroatom, and Volume 11 deals with 5:5 and 5:6 fused rings systems with at least one ring junction nitrogen, while Volume 12 is devoted to all other systems of five and/or six-membered fused or spiro heterocyclic rings with ring junction heteroatoms. Volumes 13 and 14: Seven-membered and larger heterocyclic rings including all their fused derivatives (except those containing three- or four-membered heterocyclic rings which are included in Volume 1 and 2, respectively). Volume 15: Author, ring and subject indexes.

8,174 citations

Journal ArticleDOI
TL;DR: 1i (4-[5-(4-methylphenyl)-3-(trifluoromethyl)- H-pyrazol-1-yl]benzenesulfonamide, SC-58635, celecoxib), which is currently in phase III clinical trials for the treatment of rheumatoid arthritis and osteoarthritis, is identified.
Abstract: A series of sulfonamide-containing 1,5-diarylpyrazole derivatives were prepared and evaluated for their ability to block cyclooxygenase-2 (COX-2) in vitro and in vivo. Extensive structure-activity relationship (SAR) work was carried out within this series, and a number of potent and selective inhibitors of COX-2 were identified. Since an early structural lead (1f, SC-236) exhibited an unacceptably long plasma half-life, a number of pyrazole analogs containing potential metabolic sites were evaluated further in vivo in an effort to identify compounds with acceptable pharmacokinetic profiles. This work led to the identification of 1i (4-[5-(4-methylphenyl)-3-(trifluoromethyl)- H-pyrazol-1-yl]benzenesulfonamide, SC-58635, celecoxib), which is currently in phase III clinical trials for the treatment of rheumatoid arthritis and osteoarthritis.

1,895 citations


"Catalyst-free, one-pot, three-compo..." refers background in this paper

  • ...The pyrazole motif makes the core structure of blockbuster drugs such as Celebrex(R) [41] and Viagra(R) [42] that act as PDE-5 inhibitors, Zoniporide [43] as sodium hydrogen ion exchanger inhibitors, 1-aryl-5-aminopyrazole as NPY5 antagonist [44], and PNU-32945 as HIV-reverse transcriptase inhibitors [45] (Fig....

    [...]

Journal ArticleDOI
TL;DR: 5-(2′-Alkoxyphenyl)pyrazolo[4,3-d]pyrimidin-7-ones, and in particular sildenafil (VIAGRATM), discovered through a rational drug design programme, are potent and selective inhibitors of the type 5 cGMP phosphodiesterase from both rabbit platelets and human corpus cavernosum.

576 citations


"Catalyst-free, one-pot, three-compo..." refers background in this paper

  • ...The pyrazole motif makes the core structure of blockbuster drugs such as Celebrex(R) [41] and Viagra(R) [42] that act as PDE-5 inhibitors, Zoniporide [43] as sodium hydrogen ion exchanger inhibitors, 1-aryl-5-aminopyrazole as NPY5 antagonist [44], and PNU-32945 as HIV-reverse transcriptase inhibitors [45] (Fig....

    [...]

Journal ArticleDOI
TL;DR: This paper details the copper-catalyzed N-arylation of pi-excessive nitrogen heterocycles and general conditions were found that tolerate functional groups such as aldehydes, ketones, alcohols, primary amines, and nitriles on the aryl halide or heterocycle.
Abstract: This paper details the copper-catalyzed N-arylation of π-excessive nitrogen heterocycles. The coupling of either aryl iodides or aryl bromides with common nitrogen heterocycles (pyrroles, pyrazoles, indazoles, imidazoles, and triazoles) was successfully performed in good yield with catalysts derived from diamine ligands and CuI. General conditions were found that tolerate functional groups such as aldehydes, ketones, alcohols, primary amines, and nitriles on the aryl halide or heterocycle. Hindered aryl halides or heterocycles were also found to be suitable substrates using the conditions reported herein.

524 citations

Journal ArticleDOI
TL;DR: Compounds 4 and 12a are the most distinctive derivatives identified in the present study because of their remarkable in vivo and in vitro anti-inflammatory potency and their pronounced antibacterial activities comparable to ampicillin against Gram positive.

372 citations