A one-pot, three-component regiospecific synthesis of dispiropyrrolidines containing a thiophenone ring via 1,3-dipolar cycloaddition reactions of azomethine ylides

Moghaddam, Firouz Matloubi; Khodabakhshi, Mohammad Reza; Ghahremannejad, Zahra; Foroushani, Behzad Koushki; Ng, Seik Weng

doi:10.1016/j.tetlet.2013.03.023

Cited by 29 publications

(6 citation statements)

References 40 publications

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“…Unsaturated thiophenone dipolarophiles 138 were reacted with azomethine ylides, generated in situ from sarcosine 9 and isatins 1, to produce the corresponding cycloadducts (Scheme 50). 96 The cycloaddition reaction was found to be highly regio-and diastereoselective. …”

Section: Scheme 49mentioning

confidence: 99%

Synthesis of spiro-fused heterocyclic scaffolds through multicomponent reactions involving isatin

Ziarani¹,

Moradi²,

Lashgari³

2015

Arkivoc

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Isatin has been utilized in many heterocyclic preparations and considered as an important building block in organic synthesis. There is a wide range of multi-component reactions that include isatin in the synthesis of heterocyclic compounds. This review highlights the advances in the use of isatin as starting material in the synthesis of various organic compounds and drugs during the period from 2012 to 2015.

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Section: Scheme 49mentioning

confidence: 99%

Synthesis of spiro-fused heterocyclic scaffolds through multicomponent reactions involving isatin

Ziarani¹,

Moradi²,

Lashgari³

2015

Arkivoc

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“…24,25 For example, Yan and co-workers reported the synthesis of spiro[indoline-3,3′-pyrrolo[1,2a]isoquinolines] by a 1,3-dipolar cycloaddition reaction of N-phenacylquinolinium bromides with 3-phenacylideneoxindoles as dipolarophiles. 24 Because of the biological importance of pyrrolo[2,1a]isoquinolines and quinoxaline structures, and in continuation of related studies and our growing interest in developing 1,3-dipolar cycloaddition reactions, [26][27][28] we decided to synthesize spiroheterocycles containing both pyrrolo[2,1a]isoquinoline and quinoxaline moieties. To the best of our knowledge, this is the first report of a 1,3-dipolar cycloaddition of N-phenacylquinolinium bromides with 1-aryl-2-(11H-indeno[1,2-b]quinoxalin-11-ylidene)ethanones in which electron-deficient alkenes act as dipolarophiles to give functionalized spiropyrrolo[2,1-a]isoquinoline derivatives bearing four stereogenic centers.…”

Section: Letter Syn Lettmentioning

confidence: 99%

Regio- and Diastereoselective Synthesis of Novel Polycyclic Pyrrolo[2,1-a]isoquinolines Bearing Indeno[1,2-b]quinoxaline Moieties by a Three-Component [3+2]-Cycloaddition Reaction

Moghaddam

Moafi

Jafari

et al. 2019

Synlett

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A regio- and diastereoselective synthesis of 2,3-dihydro-10b′H-spiro[indeno[1,2-b]quinoxaline-11,1′-pyrrolo[2,1-a]isoquinoline]-2′,3′-diylbis(phenylmethanone) derivatives containing four contiguous chiral stereocenters was achieved through 1,3-dipolar cycloaddition of isoquinolinium N-ylides in a one-pot three-component reaction. The desired products were obtained in short reaction times and in moderate to high yields (up to 92%) under relatively mild reaction conditions. The structure and relative stereochemistry of the desired product was confirmed by X-ray diffraction analysis.

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“…2022, 12, 360 [12], antimycobacterial [13], antimicrobial and anticancer activities (Figure 1) [14-17 thermore, they are also known for acetylcholinesterase inhibition [18,19]. Among the current methodologies for the synthesis of spiro[oxindole-2,3′-p dine] derivatives, multicomponent (3+2) cycloaddition reactions (MCRs) of electron cient exocyclic alkenes with azomethine ylides, generated in situ by decarboxylativ densation of isatin derivatives with α-aminoacids, have emerged as one of the mos erful tools (Scheme 1, Equation ( 1)) [20][21][22][23][24][25][26][27]. However, a thorough literature survey decarboxylative process reveals that L-valine received only little attention as a comp in the formation of azomethine ylides (Scheme 1, Equation ( 2)).…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial Activity and In Silico Molecular Docking Studies of Pentacyclic Spiro[oxindole-2,3′-pyrrolidines] Tethered with Succinimide Scaffolds

et al. 2021

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Three-component cascade reactions of (E)-3-arylidene-1-methyl-pyrrolidine-2,5-diones, L-valine and various isatin derivatives are described. A series of 17 spiropyrrolidine derivatives with wide structural complexity and diversity have been thus obtained in moderate to excellent yields under mild reaction conditions. The structure and stereochemistry of these N-heterocyclic cycloadducts has been established by spectroscopic techniques and unambiguously confirmed by a single-crystal X-ray diffraction analysis performed on one derivative. UV-visible spectra have been recorded for all new compounds. Furthermore, the synthesized N-heterocyclic compounds have been screened for their in vitro antibacterial and antifungal activities. Several derivatives exhibited moderate to good activities, comparable to those of the known standard drugs Amphotericin B and Tetracycline. Structural activity relationships (SARs) and molecular docking of the most promising derivatives into the binding sites of glucosamine 6-phosphate synthase (GlcN6P) and methionyl-trna-synthetase (1PFV) were also established. Furthermore, pharmacokinetic studies indicate that the heterocycles exhibit acceptable predictive ADMET (absorption, distribution, metabolism, excretion, and toxicity) properties and good drug ability.

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A one-pot, three-component regiospecific synthesis of dispiropyrrolidines containing a thiophenone ring via 1,3-dipolar cycloaddition reactions of azomethine ylides

Cited by 29 publications

References 40 publications

Synthesis of spiro-fused heterocyclic scaffolds through multicomponent reactions involving isatin

Synthesis of spiro-fused heterocyclic scaffolds through multicomponent reactions involving isatin

Regio- and Diastereoselective Synthesis of Novel Polycyclic Pyrrolo[2,1-a]isoquinolines Bearing Indeno[1,2-b]quinoxaline Moieties by a Three-Component [3+2]-Cycloaddition Reaction

Antimicrobial Activity and In Silico Molecular Docking Studies of Pentacyclic Spiro[oxindole-2,3′-pyrrolidines] Tethered with Succinimide Scaffolds

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