One pot, three component 1,3 dipolar cycloaddition: Regio and diastereoselective synthesis of spiropyrrolidinyl indenoquinoxaline derivatives

Pattanaik, Priyabrata; Nayak, Smita; Mishra, Deepak R.; Panda, Pravati; Raiguru, Bishnu Prasad; Mishra, Nilima Priyadarsini; Mohapatra, Seetaram; Mallampudi, N. Arjunreddy; Purohit, Chandra Shekhar

doi:10.1016/j.tetlet.2018.05.087

Cited by 23 publications

(16 citation statements)

References 21 publications

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“…This reaction is diastereoselective, with a 1,3-dipolar cycloaddition of azomethine ylide with chromene-3-carbonitrile, only one endo products 288 and 289 is obtained (Scheme 75). [271] An easily obtainable from indenoquinoxalin-2-one 281 semi-or (thiosemi)carbazones 290 at boiling in acetic anhydride underwent cyclization yielding spiro indenoquinoxalines 291 (Scheme 76). [282]…”

Section: The Strategy Of Direct Spirocycle Buildup To Molecule Of Indmentioning

confidence: 99%

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Advances in the Synthesis of Benzo‐Fused Spiro Nitrogen Heterocycles: New Approaches and Modification of Old Strategies

Гатауллин

2020

Helvetica Chimica Acta

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The review covers the results of studies published in the literature on the synthesis of spiro-linked heterocycles of the indole, quinoline, benzoxazine, benzothiazine, indenoquinoxaline, pyridopyrimidine, and acridine series. Possible approaches to the synthesis of spirocycles through a sequence of well-known Knoevenagel, Michael reactions, deamination cyclization of 1,2-dicarbonyl, CH-acid compounds, direct cycloaddition of activated olefins to isatins, 3-alkylideneindoles, 2-oxindoles, in situ generated azomethine ylides, indenoquinoxalines are analyzed. Attention is drawn to approaches to the preparation of spiro-fused compounds using reactions of intra-and intermolecular dearomatization of indoles. Recent advances in the synthesis of spiro-linked benzo heterocycles from derivatives of 2-olefin substituted anilines are summarized. The examples of the synthesis of spiro-fused heterocycles by means of metal complexes catalyzed decomposition of diazo compounds are given. Some syntheses of biologically active representatives are shown, as well as the use of transformations of spiroheterocycles in the preparation of other heterocycles.

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Section: The Strategy Of Direct Spirocycle Buildup To Molecule Of Indmentioning

confidence: 99%

“…Benzo‐fused heterocycles with a structure of quinoline, quinoxaline, acridine or indenoquinoxaline are found in both synthetic and natural biologically active compounds, which are of great interest to a large number of researchers [268–272] …”

Section: Synthesis Of Spirocyclic Quinoxaline Acridine Benzoxazinementioning

confidence: 99%

Advances in the Synthesis of Benzo‐Fused Spiro Nitrogen Heterocycles: New Approaches and Modification of Old Strategies

Гатауллин

2020

Helvetica Chimica Acta

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“…Recently, Nayak et al .employed 1,3‐dipolar cycloaddition strategy for the construction of indenoquinoxaline grafted spiropyrrolidine linked chromene conjugates 52/53 . These complex molecular frameworks were developed from indenoquinoxaline 39 , proline 49 /benzyl amine 50 and chromene‐3‐carbonitrile 51 in ethanol under conventional heating as well as microwave conditions (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Ninhydrin Adducts as Valid Synthon in Organic Synthesis: A Review

Das¹,

Dutta

2020

ChemistrySelect

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Ninhydrin (1,2,3‐indanetrione hydrate) is a powerful electrophile having enormousapplications in organic and bio‐organic sciences. In the last few years, reactivity of various ninhydrin adducts have been exploited extensively for the development of diverse organic scaffolds. The present review focuses on the applications of readily accessible ninhydrin adducts as building block towards the synthesis of a variety of compounds including N‐inserted compounds, spiro‐heterocycles, medium ring compounds, polycyclic molecules, propellanes, cycloadducts, allylic anions, axially chiral molecules etc. Interestingly, some of the compounds have profound biological activities and a few display important photophysical properties. Most of the reactions described here are simple and carried out with easily available starting materials under green conditions.

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“…[45,46] With the extension of our current work, [22,[47][48][49][50] considering the importance in addition to potency of pyrrole as well as 2H-chromene molecules, we have shaped a strategy for promising molecules. Because of this advantage, this technique has gained much more significance in the field of synthetic as well as medicinal chemistry.…”

Section: Introductionmentioning

confidence: 99%

Microwave‐assisted rapid and efficient synthesis of chromene‐fused pyrrole derivatives through multicomponent reaction and evaluation of antibacterial activity with molecular docking investigation

Baral

Mishra

et al. 2019

Journal of Heterocyclic Chem

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The current study aimed to identify a new strategy of FeCl 3 catalyzed multicomponent synthesis of substituted 2H-chromene-fused pyrrole derivatives.A series of chromene-based pyrrole prepared by employing an array of 3-nitro-2H-chromenes, aniline, and acetylacetone in toluene under microwave irradiation. Using FeCl 3 as a prompt catalyst and microwave irradiation to synthesize 2H-chromene-fused pyrrole motifs significantly reduces the reaction time and facilitates to high yields (83%-95%). Structure of all synthesized compounds analyzed by spectroscopic analysis. One-pot reaction, short reaction period, and simple experimental procedure are the fascinating properties associated with this protocol. The in vitro antibacterial activity of the entire series was assessed against Staphylococcus aureus and Escherichia coli. Out of all the compounds, 15b and 15h revealed most excellent potency against both the bacterial strains relative to the reference gentamicin. Docking study was employed to determine the possible binding orientation of DNA gyrase with the active sites of chromene-fused pyrrole analog. The docking results show that compounds 15b and 15h have higher binding affinity with energy −8.00 and −8.80 kcal/mol. These results illuminate the mode of binding progression and provide an esteemed pathway for the design and the structural modification of chromene-fused pyrroles as a newly advanced class of antibacterial agent.

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One pot, three component 1,3 dipolar cycloaddition: Regio and diastereoselective synthesis of spiropyrrolidinyl indenoquinoxaline derivatives

Cited by 23 publications

References 21 publications

Advances in the Synthesis of Benzo‐Fused Spiro Nitrogen Heterocycles: New Approaches and Modification of Old Strategies

Advances in the Synthesis of Benzo‐Fused Spiro Nitrogen Heterocycles: New Approaches and Modification of Old Strategies

Ninhydrin Adducts as Valid Synthon in Organic Synthesis: A Review

Microwave‐assisted rapid and efficient synthesis of chromene‐fused pyrrole derivatives through multicomponent reaction and evaluation of antibacterial activity with molecular docking investigation

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