A new efficient synthesis of highly functionalized alizarins from alizarin, acetylenic esters, and isocyanides

Azad, Leila; Sanaeishoar, Haleh; Yavari, Issa

doi:10.1007/s00706-015-1643-0

Cited by 5 publications

(4 citation statements)

References 18 publications

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“…After the addition of the isocyanide to the alkyne, a zwitterionic nitrilium‐carbanion intermediate is produced, which can act as a base for activating pronucleophilic species (NuH). Recently, Yavari discovered that alizarin could be transformed into a six‐membered ring‐fused structure via the cyclization of the ketenimine intermediate 26 …”

Section: Activation Of the Isocyanides With Electrophilic Componentmentioning

confidence: 99%

“…Recently, Yavari discovered that alizarin could be transformed into a six-membered ring-fused structure via the cyclization of the ketenimine intermediate. 26 The combination of an electrophile and a Lewis acid is another method to activate the terminal carbon of the isocyanide. However, the choice of a Lewis acid is crucial owing to the competing polymerization and uncontrolled insertion of the isocyanide toward the electrophile.…”

Section: Activation By Other Electrophilic Partnersmentioning

confidence: 99%

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Organic transformations of isocyanides classified by their activation strategies

Kim

Hong

2023

Bulletin Korean Chem Soc

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Isocyanides have been extensively utilized in organic synthesis to construct valuable chemical structures. Classical Ugi 4‐component reaction is the robust method to access diversely functionalized peptoids. By using well‐established cyclization techniques, a variety of nitrogen heterocycles from commercially accessible compounds have been efficiently synthesized. Several transition metal‐catalyzed processes have been developed to utilize isocyanide as a useful carbonyl nitrogen synthon. Recently developed synthetic methods, such as C–H bond activation and visible‐light photocatalysis, have been adopted to the isocyanide chemistry to enhance the efficiency, availability, and novelty of the chemical processes. This review summarizes the reactivity of isocyanide classified by the activation modes of electrophilic, nucleophilic, and radical species, together with the seminal discoveries and recent advances in the past 10 years.

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Section: Activation Of the Isocyanides With Electrophilic Componentmentioning

confidence: 99%

Section: Activation By Other Electrophilic Partnersmentioning

confidence: 99%

Organic transformations of isocyanides classified by their activation strategies

Kim

Hong

2023

Bulletin Korean Chem Soc

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“…Also, ethyl 4-alkyl(aryl)imino-4-(9,10-dihydro-1-hydroxy-9,10-dioxoanthracen-2-yloxy)but-2-enoates were obtained when ethyl propiolate was used as the active acetylene. 94…”

Section: Scheme 87 Synthesis Of Arylthioacrylates Thiazines and Thiaz...mentioning

confidence: 99%

Acetylenic Esters in Organic Synthesis

Hajinasiri¹

2022

Synlett

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Activated acetylenic substrates such as acetylenic esters and alkyl propiolates are very important in organic synthesis. Due to their electron deficiency, these compounds are widely used in combinatorial and multicomponent reactions, enabling the synthesis of a large variety of novel compounds. In addition, these substrates are powerful Michael acceptors and convenient dienophiles and dipolarophiles in Diels–Alder and 1,3-dipolar cycloaddition reactions. The addition of different nucleophiles, primarily phosphorus, nitrogen or sulfur, to the triple bonds of these substrates produces key intermediates, such as Tebby and Huisgen zwitterions, which can lead to designing pathways toward the generation of spirocyclic and polycyclic compounds. This account highlights recent studies on the chemistry of acetylenic esters and their applications in organic synthesis.1 Introduction2 Synthesis of Acyclic and Monocyclic Compounds3 Synthesis of Spirocyclic Compounds4 Synthesis of Polycyclic Compounds5 Conclusion

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“…13 It has been shown that these types of zwitterions can be trapped by a variety of organic acids. [14][15][16][17] In continuation of current interest in the development of new routes to heterocyclic and carbocyclic systems, [18][19][20][21][22][23][24][25][26] we became interested in developing novel and efficient methods to construct the new 1,2-dihydroisoquinoline-based structures, with a hope of finding active hits for our particular biological assays. Herein, we report a synthesis of 1,2-dihydroisoquinolines via the three-component reaction of isoquinoline, alkyl propiolates, and CH-acids, under mild reaction conditions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of functionalized 1,2-dihydroisoquinolines via one-pot reactions of isoquinoline, alkyl propiolate, and thiazolidin-2,4-dione

Azad

Ghazvini

Sanaeishoar

et al. 2019

Journal of Chemical Research

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The reactive zwitterionic intermediates, generated from addition of isoquinoline to alkyl propiolates, react with thiazolidin-2,4-dione to afford 3-[1-(2,4-dioxothiazolidin-3-yl)isoquinolin-2(1 H)-yl]acrylates in good yields. Using (Z)-5-arylidenethiazolidine-2,4-diones as the NH-acidic component leads to 3-{1-[( Z)-5-benzylidene-2,4-dioxothiazolidin-3-yl] isoquinolin-2(1 H)-yl}acrylates in moderate to good yields in the absence of any catalysts under mild reaction conditions. The reaction between quinoline, ethyl propiolate, and thiazolidin-2,4-dione leads to ethyl 3-[2-(2,4-dioxothiazolidin-3-yl) quinolin-1(2 H)-yl]acrylate.

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A new efficient synthesis of highly functionalized alizarins from alizarin, acetylenic esters, and isocyanides

Cited by 5 publications

References 18 publications

Organic transformations of isocyanides classified by their activation strategies

Organic transformations of isocyanides classified by their activation strategies

Acetylenic Esters in Organic Synthesis

Synthesis of functionalized 1,2-dihydroisoquinolines via one-pot reactions of isoquinoline, alkyl propiolate, and thiazolidin-2,4-dione

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