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

Tripathi, Bhartendu Pati; Mishra, Anu; Rai, Pragati; Pandey, Yogesh; Srivastava, M. P.; Yadav, Snehlata; Singh, Jaya; Singh, Jagdamba

doi:10.1039/c7nj01688c

Cited by 44 publications

(15 citation statements)

References 55 publications

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“…Multicomponent reactions (MCRs), or one-pot reactions in which at least three different substrates join through the covalent bonds, have been of great interest in synthetic organic chemistry due to the efficiency of giving higher overall yields (Musonda et al, 2004;Dekamin et al, 2013a,b;Dekamin and Eslami, 2014;Rotstein et al, 2014;Sudhapriya et al, 2014;Oshiro et al, 2015;Aly, 2016;Aly et al, 2018). A literature survey reveals that numerous methods were developed for the synthesis of dihydropyrano[2,3-c]pyrazoles (Sudhapriya et al, 2014;Ambethkar et al, 2015;Pati Tripathi et al, 2017). In the beginning, we synthesized the reported pyrano-pyrazole 1 as a staring material by using ethylacetoacetate, hydrazine hydrate, 2-bromobenzaldehyde, and malononitrile, and the reaction was performed in ethanol using triethylamine as basic catalyst (Muramulla and Zhao, 2011).…”

Section: Chemistrymentioning

confidence: 99%

Novel Anticancer Fused Pyrazole Derivatives as EGFR and VEGFR-2 Dual TK Inhibitors

et al. 2020

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EGFR and VEGFR-2 represent promising targets for cancer treatment as they are very important in tumor development as well as in angiogenesis and metastasis. In this work, 6-amino-4-(2-bromophenyl)-3-methyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile 1 and (E)-4-(2-Bromobenzylidene)-5-methyl-2,4-dihydro-3H-pyrazol-3-one 11 were selected as starting materials to synthesize different fused pyrazole derivatives; dihydropyrano[2,3-c]pyrazole 1, 2, 7-9, and 15, pyrazolo[4 ′ ,3 ′ :5,6]pyrano[2,3d]pyrimidine 3-6, pyrazolo[3,4-d]pyrimidine 12 and 13, and pyrazolo[3,4-c]pyrazole 14 derivatives were synthesized to evaluate their anticancer activity against HEPG2 human cancer cell lines compared to erlotinib and sorafenib as reference drugs. Seven compounds 1, 2, 4, 8, 11, 12, and 15 showed nearly 10 fold higher activity than erlotinib (10.6 µM) with IC 50 ranging from 0.31 to 0.71 µM. In vitro EGFR and VEGFR-2 inhibitory activity were performed for the synthesized compounds, and the results identified compound 3 as the most potent EGFR inhibitor (IC 50 = 0.06 µM) and compound 9 as the most potent VEGFR-2 inhibitor (IC 50 = 0.22 µM). Moreover, compounds 9 and 12 revealed potent dual EGFR and VEGFR-2 inhibition, and these results were supported by docking studies of these two compounds within the active sites of both enzymes.

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Section: Chemistrymentioning

confidence: 99%

Novel Anticancer Fused Pyrazole Derivatives as EGFR and VEGFR-2 Dual TK Inhibitors

et al. 2020

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“…In support of our proposition for this radical pathway, we conducted sets of control experiments with our model reaction in the presence of radical‐trapping reagents (TEMPO and p ‐benzoquinone) (Table ). It was observed that the formation of product 3‐1 was completely prohibited in case of using at least two equivalents of TEMPO or one equivalent of p ‐benzoquinone, thereby suggesting the involvement of a radical process in the transformation …”

Section: Resultsmentioning

confidence: 99%

sp2‐C–H Acetoxylation of Diversely Substituted (E)‐1‐(Arylmethylene)‐2‐phenylhydrazines Using PhI(OAc)₂ as Acetoxy Source at Ambient Conditions

Brahmachari

Karmakar

2019

Eur J Org Chem

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A catalyst‐ and additive‐free simple and straightforward method for regioselective direct sp2 C–H acetoxylation reaction of aldehyde hydrazones has been achieved at ambient temperature employing PIDA as an acetoxy source. The scope of the reaction has been successfully verified with a wide range of biologically important aldehyde hydrazones with diverse functional group tolerance. The method is highly selective, mild and efficient, operationally simple, rapid and high‐yielding.

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“…Low yields (or traces) of the final adduct were observed under several catalyst-free conditions (see cited references). Efforts to develop catalyzed conditions have, however, been dedicated [ 86 , 87 , 88 , 89 ] to this important MCR transformation. Many of these catalytic systems required at least one reagent in excess [ 90 , 91 , 92 , 93 , 94 ], thus working against the desirable green and sustainable conditions anticipated for MCRs.…”

Section: Catalyst-free Mcrs and Reasons To Use Catalystsmentioning

confidence: 99%

Catalytic Approaches to Multicomponent Reactions: A Critical Review and Perspectives on the Roles of Catalysis

2021

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In this review, we comprehensively describe catalyzed multicomponent reactions (MCRs) and the multiple roles of catalysis combined with key parameters to perform these transformations. Besides improving yields and shortening reaction times, catalysis is vital to achieving greener protocols and to furthering the MCR field of research. Considering that MCRs typically have two or more possible reaction pathways to explain the transformation, catalysis is essential for selecting a reaction route and avoiding byproduct formation. Key parameters, such as temperature, catalyst amounts and reagent quantities, were analyzed. Solvent effects, which are likely the most neglected topic in MCRs, as well as their combined roles with catalysis, are critically discussed. Stereocontrolled MCRs, rarely observed without the presence of a catalytic system, are also presented and discussed in this review. Perspectives on the use of catalytic systems for improved and greener MCRs are finally presented.

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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

Abstract: Visible light mediated, an eco-friendlier synthetic protocol for dihydropyrano[2,3-c]pyrazoles via catalyst-free and solvent-free conditions at room temperature.

Cited by 44 publications

References 55 publications

Novel Anticancer Fused Pyrazole Derivatives as EGFR and VEGFR-2 Dual TK Inhibitors

Novel Anticancer Fused Pyrazole Derivatives as EGFR and VEGFR-2 Dual TK Inhibitors

sp2‐C–H Acetoxylation of Diversely Substituted (E)‐1‐(Arylmethylene)‐2‐phenylhydrazines Using PhI(OAc)₂ as Acetoxy Source at Ambient Conditions

Catalytic Approaches to Multicomponent Reactions: A Critical Review and Perspectives on the Roles of Catalysis

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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

Abstract: Visible light mediated, an eco-friendlier synthetic protocol for dihydropyrano[2,3-c]pyrazoles via catalyst-free and solvent-free conditions at room temperature.

Cited by 44 publications

References 55 publications

Novel Anticancer Fused Pyrazole Derivatives as EGFR and VEGFR-2 Dual TK Inhibitors

Novel Anticancer Fused Pyrazole Derivatives as EGFR and VEGFR-2 Dual TK Inhibitors

sp2‐C–H Acetoxylation of Diversely Substituted (E)‐1‐(Arylmethylene)‐2‐phenylhydrazines Using PhI(OAc)2 as Acetoxy Source at Ambient Conditions

Catalytic Approaches to Multicomponent Reactions: A Critical Review and Perspectives on the Roles of Catalysis

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sp2‐C–H Acetoxylation of Diversely Substituted (E)‐1‐(Arylmethylene)‐2‐phenylhydrazines Using PhI(OAc)₂ as Acetoxy Source at Ambient Conditions