Synthesis of Spiro[indoline‐3,4′‐pyrano[3,2‐<i>c</i>]chromene]diones

Ghadiri, Sakineh; Bayat, Mohammad; Hosseini, Fahimeh Sadat

doi:10.1002/jhet.3326

Cited by 7 publications

(2 citation statements)

References 23 publications

(20 reference statements)

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“…Another achievement for the synthesis of amino‐substituted spiro‐pyrano[3,2‐ c ]coumarin has been gained by Ghadiri and co‐workers in 2018 (Scheme 50). [120] The synthesis involves the three‐component reaction of 4‐hydroxycoumarin 1 , isatin 116 , and N‐ alkyl‐1‐(methylthio)‐2‐nitroethenamine derived from various amines 4 and nitroketenedithioacetal 119 in presence of ethanol as the solvent under catalyst and metal‐free conditions. A wide variety of substituted isatins and amines were undergoing the reaction smoothly to give the desired products in 70–84% yield.…”

Section: Synthesis Of Six‐membered Heterocycles Via Metal‐free Multic...mentioning

confidence: 99%

4‐Hydroxycoumarin: A Versatile Substrate for Transition‐metal‐free Multicomponent Synthesis of Bioactive Heterocycles

2021

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One-pot multi-component reactions especially under transition-metal-free catalysis served as an efficient, and environmentally friendly method for the construction of value-added compounds. Their importance in organic synthesis has drastically increased due to their operational simplicity, cost-effectiveness, step-and pot-economic nature. On the other hand, the molecular hybridization concept has recently emerged as a key fascinating area in medicinal and organic chemistry for the design of new drugs. Owing to the widespread occurrence in natural products, and pharmaceutical agents, the incorporation of another heterocycle either as substituents or as a fused material into 4-hydroxycoumarin moiety offers new opportunities for the broad application of the targeted coumarin-heterocycles into many branches of chemistry. Considering the importance of both the topics, here we have reviewed the developments achieved in the synthesis of diverse medicinally privileged oxygen, and nitrogen-containing heterocycles as well as spiro-heterocycles either linked or fused with coumarin moiety by using readily accessible 4-hydroxycoumarin as the starting material via one-pot multi-component reaction under transition-metalfree conditions.[a] B. Borah, K.

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Section: Synthesis Of Six‐membered Heterocycles Via Metal‐free Multic...mentioning

confidence: 99%

4‐Hydroxycoumarin: A Versatile Substrate for Transition‐metal‐free Multicomponent Synthesis of Bioactive Heterocycles

2021

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“…The intramolecular condensation in this compound with the separation of methyl mercaptan CH 3 SH completes the formation of spirocycle 48 ( Scheme 15). [137] …”

Section: Strategy For Creating a Spirocarbon Center On The Isatin Bacmentioning

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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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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Six-Membered Ring Systems: With O and/or S Atoms

Santos¹,

Silva²

2020

Progress in Heterocyclic Chemistry

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This book and the individual contributions contained in it are protected under copyright by the Publisher (other than as may be noted herein). NoticesKnowledge and best practice in this field are constantly changing. As new research and experience broaden our understanding, changes in research methods, professional practices, or medical treatment may become necessary.Practitioners and researchers must always rely on their own experience and knowledge in evaluating and using any information, methods, compounds, or experiments described herein. In using such information or methods they should be mindful of their own safety and the safety of others, including parties for whom they have a professional responsibility.

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Synthesis of Spiro[indoline‐3,4′‐pyrano[3,2‐c]chromene]diones

Cited by 7 publications

References 23 publications

4‐Hydroxycoumarin: A Versatile Substrate for Transition‐metal‐free Multicomponent Synthesis of Bioactive Heterocycles

4‐Hydroxycoumarin: A Versatile Substrate for Transition‐metal‐free Multicomponent Synthesis of Bioactive Heterocycles

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

Six-Membered Ring Systems: With O and/or S Atoms

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