Synthesis of Novel Spirooxindole Derivatives Using N-Phenylpiperazine as an Organocatalyst

Mahdavi, Saeed; Habibi, Azizollah; Dolati, Hadi; Nasab, Saber Hakimi; Shahcheragh, Seyyed Mohammad

doi:10.2174/1570178613666160229224626

Cited by 4 publications

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“…[1] Polycyclic fused pyrans are considered as one of the most important classes of heterocycles considering their various medicinal properties such as anti-inflammatory, [2] antibacterial, [3] anti-platelet aggregation activity, [4] anticancer, [5] antitumour, [6] anti-human immunodeficiency virus activity [7] and antiplasmodial activity. [8] Fused pyrans also exhibit antiproliferative activity, [9][10] antimicrobial activity, [11][12][13] antituberculosis and antimalarial activity. [14] A few representative examples of bioactive fused pyran derivatives are shown in Figure 1.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Pentacyclic Pyran Fused Pyrazolo Benzo[h]quinolines by Multicomponent Reaction and Their Photophysical Studies

et al. 2022

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Herein we report for the first time a one-pot method for the synthesis of pentacyclic pyran fused pyrazolo benzo[h]quinolines in acetic acid medium from the threecomponent reaction of 2-hydroxy-1,4-naphthoquinone, α, βunsaturated aldehydes and 5-aminopyrazoles under the reflux conditions. In this reaction, four new bonds (2 CÀ C, 1 CÀ N and 1 CÀ O) and two new rings (pyridine and pyran) were formed in one-pot. The novel products contain four bioactive moieties such as pyran, pyridine, pyrazole and α-naphthol. The salient features of this method are: one-pot process, short reaction time, easier purification, no need of column chromatography and good yields of the products. All the products were characterized by IR, NMR and HRMS. Most of our synthesized compounds were found highly fluorescent. Therefore, we further studied their photophysical properties by UV-Visible and Fluorescence spectroscopy. We have calculated their quantum yields which were found in the range 0.243-0.424 in CHCl 3 solution (c = 10 À 5 M). Compound 4 e showed the highest quantum yield of 0.424.

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Section: Introductionmentioning

confidence: 99%

Synthesis of Pentacyclic Pyran Fused Pyrazolo Benzo[h]quinolines by Multicomponent Reaction and Their Photophysical Studies

et al. 2022

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“…to exhibit several potentials such as antimicrobial, 18 anticoagulant, antit-tyrosinase, 19 α-amylase, 20 anti-soybean lipoxygenase, anti-xanthine oxidase, cytotoxic, 21 and antiviral activities (Figure 2-A, 22…”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of New Quinoline Linked to Pyranotriazolopyrimidines Conjugates as Novel Targets to Discover Promising Anti-SARS-COV-2

Jannet¹,

Algethami²,

Jlizi³

et al. 2022

HETEROCYCLES

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Simple one-pot synthesis of 2-aminopyranoquinoline-3-carbonitriles 2a-d at room temperature from available 8-hydroxyquinaldine, malononitrile, and substituted aromatic aldehydes was realized. Compounds 2a-d were converted into imino ethers 3a-d, condensed with a series of hydrazide under microwave irradiation to yield novel pyranotriazolopyrimidines fused to quinoline 4a-f. Compound 4c, with a cyanomethyl group, was treated with some salicylic arylaldehydes to give the corresponding new pyranotriazolopyrimidine-chromen hybrids 5a-c in good yields. Finally a new series of arylidenes linked to triazolopyrimidopyrano[3,2-h]quinoline 6a-h were designed and synthesized by the reaction of 4a,c, both bearing a cyanomethyl group, with a series of arylaldehydes. The structures of all the compounds were evidenced by 1 H/ 13 C NMR, IR, and ESI-HRMS. The present study focuses also to predict the theoretical assembly of the COVID-19 protease (SARS-CoV-2 M pro ) and to find in advance whether this protein can be targeted by the compounds 4c, 4f, 5a-c and 6a-h thus synthesized. The docking scores of these compounds were compared to that of the co-crystallized native ligand inhibitor (N3) used as a reference standard.

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“…Quinoxaline derivatives are also biologically active heterocycles that are known to be antimetabolism, antifungal, antidepressant, antitumor, antioxidant, anticancer, and antitubercular ] agents. Several methods have been reported for the preparation of these two biologically active moieties . In addition, indene derivatives have attracted much interest due to their anti‐inflammatory, analgesic, and antibacterial properties .…”

Section: Introductionmentioning

confidence: 99%

“…Several methods have been reported for the preparation of these two biologically active moieties. [25][26][27][28][29][30] In addition, indene derivatives have attracted much interest due to their anti-inflammatory, analgesic, and antibacterial properties. [31] Therefore, the synthesis of compounds having various pharmacophores, such as pyran, quinoxaline, and indole, is very important and they can exhibit unique pharmaceutical properties.…”

Section: Introductionmentioning

confidence: 99%

The application of copolymer‐coated graphene oxide‐Fe₃O₄ in the highly efficient synthesis of 2′‐aminospiro[indeno[1,2‐b]quinoxaline‐11,4′‐[4'H] pyran]‐3′‐carbonitrile and 2′‐aminospiro[indeno‐2,4′‐[4'H]pyran]‐3′‐carbonitrile

Hojati

Amiri

Fardi

2020

Applied Organom Chemis

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A magnetic nanocomposite based on graphene oxide was prepared. Fe3O4 nanoparticles were loaded on graphene oxide sheets and GO‐Fe3O4 was covered by aniline‐pyrrole copolymer to afford poly(Py‐co‐Ani)@GO‐Fe3O4. This nanocomposite was characterized by Fourier transform infrared spectroscopy, transmission electron microscopy, vibrating sample magnetometry, X‐ray diffraction, thermogravimetric analysis, and X‐ray photoelectron spectroscopy techniques, and its catalytic activity was evaluated in the multicomponent synthesis of 2′‐aminospiro[indeno[1,2‐b]quinoxaline‐11,4′‐[4'H]pyran]‐3′‐carbonitrile and 2′‐aminospiro[indeno‐2,4′‐[4'H]pyran]‐3′‐carbonitrile derivatives. This magnetically separable catalyst is heterogeneous noncorrosive, highly efficient, and reusable.

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Synthesis of Novel Spirooxindole Derivatives Using N-Phenylpiperazine as an Organocatalyst

Cited by 4 publications

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Synthesis of Pentacyclic Pyran Fused Pyrazolo Benzo[h]quinolines by Multicomponent Reaction and Their Photophysical Studies

Synthesis of Pentacyclic Pyran Fused Pyrazolo Benzo[h]quinolines by Multicomponent Reaction and Their Photophysical Studies

Design and Synthesis of New Quinoline Linked to Pyranotriazolopyrimidines Conjugates as Novel Targets to Discover Promising Anti-SARS-COV-2

The application of copolymer‐coated graphene oxide‐Fe₃O₄ in the highly efficient synthesis of 2′‐aminospiro[indeno[1,2‐b]quinoxaline‐11,4′‐[4'H] pyran]‐3′‐carbonitrile and 2′‐aminospiro[indeno‐2,4′‐[4'H]pyran]‐3′‐carbonitrile

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Synthesis of Novel Spirooxindole Derivatives Using N-Phenylpiperazine as an Organocatalyst

Cited by 4 publications

References 0 publications

Synthesis of Pentacyclic Pyran Fused Pyrazolo Benzo[h]quinolines by Multicomponent Reaction and Their Photophysical Studies

Synthesis of Pentacyclic Pyran Fused Pyrazolo Benzo[h]quinolines by Multicomponent Reaction and Their Photophysical Studies

Design and Synthesis of New Quinoline Linked to Pyranotriazolopyrimidines Conjugates as Novel Targets to Discover Promising Anti-SARS-COV-2

The application of copolymer‐coated graphene oxide‐Fe3O4 in the highly efficient synthesis of 2′‐aminospiro[indeno[1,2‐b]quinoxaline‐11,4′‐[4'H] pyran]‐3′‐carbonitrile and 2′‐aminospiro[indeno‐2,4′‐[4'H]pyran]‐3′‐carbonitrile

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The application of copolymer‐coated graphene oxide‐Fe₃O₄ in the highly efficient synthesis of 2′‐aminospiro[indeno[1,2‐b]quinoxaline‐11,4′‐[4'H] pyran]‐3′‐carbonitrile and 2′‐aminospiro[indeno‐2,4′‐[4'H]pyran]‐3′‐carbonitrile