Journal ArticleDOI
Synthesis and some properties of 6-di(tri)fluoromethyl- and 5-di(tri)fluoroacetyl-3-methyl-1-phenylpyrano[2,3-c]pyrazol-4(1H)-ones
V. Ya. Sosnovskikh,Mikhail A. Barabanov,Boris I. Usachev,Roman A. Irgashev,Vladimir S. Moshkin +4 more
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TLDR
In this article, the reaction of pyrano-pyrazoles with hydrazine hydrate, ethyl mercaptoacetate, or aromatic amines proceed at the C(6) atom with pyrone ring opening and formation of aminoenones, pyrazoles, or thiophenes with the 5-hydroxy-3-methyl-1-phenyl-4 -pyrazolyl fragment.Abstract:
Condensation of 4-acetyl-5-hydroxy-3-methyl-1-phenylpyrazole with RFCO2Et (RF = CF2H, CF3) in the presence of LiH affords 4-di(tri)fluoroacetoacetyl-5-hydroxy-3-methyl-1-phenylpyrazoles from which 6-di(tri)fluoromethyl-and 5-di(tri)fluoroacetyl-3-methyl-1-phenylpyrano[2,3-c]pyrazol-4(1H)-ones were synthesized. The reactions of pyrano-pyrazoles with hydrazine hydrate, ethyl mercaptoacetate, or aromatic amines proceed at the C(6) atom with pyrone ring opening and formation of aminoenones, pyrazoles, or thiophenes with the 5-hydroxy-3-methyl-1-phenyl-4-pyrazolyl fragment.read more
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Journal ArticleDOI
Solvent-free multicomponent synthesis of pyranopyrazoles: per-6-amino-β-cyclodextrin as a remarkable catalyst and host
TL;DR: In this article, a simple, green and efficient protocol was developed with per-6-amino-β-cyclodextrin (per-6ABCD) which acts simultaneously as a supramolecular host and as an efficient solid base catalyst for the solvent-free syntheses of various dihydropyrano[2,3-c ]pyrazole derivatives involving a four-component reaction.
Journal ArticleDOI
A green and clean pathway: one pot, multicomponent, and visible light assisted synthesis of pyrano[2,3-c]pyrazoles under catalyst-free and solvent-free conditions
Bhartendu Pati Tripathi,Anu Mishra,Pratibha Rai,Yogesh Kumar Pandey,Madhulika Srivastava,Snehlata Yadav,Jaya Singh,Jagdamba Singh +7 more
TL;DR: A mild, eco-efficient and metal-free synthetic protocol for the production of biologically significant scaffold dihydropyrano[2,3-c]pyrazoles via reaction between ethylacetoacetate (1), hydrazine hydrate (2), aromatic aldehydes (3) and malononitrile (4) exploiting visible light as a reaction promoter has been developed.
Journal ArticleDOI
Green synthesis of 1,4-dihydropyrano[2,3-c]pyrazole derivatives using maltose as biodegradable catalyst
Mehrnoosh Kangani,Nourallah Hazeri,Malek Taher Mghsoodlou,Sayyed Mostafa Habibi-Khorasani,Sajjad Salahi +4 more
TL;DR: In this paper, a simple and efficient method for one-pot four-component synthesis of highly functionalized 1,4-dihydropyrano[2,3-c]pyrazoles using hydrazine monohydrate or phenylhydrazine, ethyl acetoacetate, malononitrile and arylaldehydes with maltose as catalyst, has been developed.
Journal ArticleDOI
An Efficient Multi-component Synthesis of 6-Amino-3-methyl-4-Aryl-2,4- dihydropyrano[2,3-c]Pyrazole-5-carbonitriles
G. Santhosh Kumar,C. Kurumurthy,B. Veeraswamy,P. Sambasiva Rao,P. Shanthan Rao,Banda Narsaiah +5 more
TL;DR: This efficient, simple, rapid, and green four-component reaction gives access to a wide range of the different substituted title compounds as discussed by the authors, and can be applied to a variety of applications.
Journal ArticleDOI
Ag NPs decked GO composite as a competent and reusable catalyst for ‘ON WATER’ chemoselective synthesis of pyrano[2,3-c:6,5-c′]dipyrazol]-2-ones
TL;DR: In this paper, Ag NPs decked GO composite was synthesized and characterized and studied its role as reusable catalyst for the ON-WATER chemoselective synthesis of pyranodipyrazolones via the reaction of different carbonyl compounds with 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one.
References
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Journal ArticleDOI
Synthesis of 4-(acylacetyl)-1-phenyl-2-pyrazolin-5-ones from 3-acyl-2H-pyran-2,4(3H)-diones. Their synthetic applications to functionalized 4-oxopyrano[2,3-c]pyrazole derivatives
Journal ArticleDOI
Synthesis and A1 and A2A adenosine binding activity of some pyrano[2,3-c]pyrazol-4-ones
Vittoria Colotta,Daniela Catarzi,Flavia Varano,Fabrizio Melani,Guido Filacchioni,Lucia Cecchi,Letizia Trincavelli,Claudia Martini,Antonio Lucacchini +8 more
TL;DR: The most selective and potent ligand among the reported compounds was the 1,4-dihydro-1-phenyl-3-methyl-6-(3-aminophenyl)-pyrano[2,3-c]pyrazol-4-ones which showed a 27-fold selectivity for A1 receptor and a Ki value of 84 nM.
Journal ArticleDOI
Synthesis of 2-(trifluoromethyl)-1,2-dihydro-4H-thieno[2,3-c]chromen-4-ones and 2-(trifluoromethyl)-4H-thieno[2,3-c]chromen-4-ones from 2-trifluoromethylchromones and ethyl mercaptoacetate
TL;DR: In this paper, the redox reaction of 2-trifluoromethylchromones with ethyl mercaptoacetate in the presence of triethylamine results in the formation of 1,2-dihydrothieno[2,3-c]chromen-4-ones and diethyl 3,4-dithiadipate in high yields.
Journal ArticleDOI
Synthesis of bipyrazoles and pyrazoloisoxazoles from 3‐acetyl‐4‐hydroxy‐6‐methyl‐2H‐pyran‐2‐one
TL;DR: In this paper, the synthesis of bipyrazoles and pyrazoloisoxazoles from 4 is reported, which is the state-of-the-art result.