Group-assisted purification chemistry principles to access highly substituted zwitterionic furans via fast, concise, and efficient one-pot three-component assembly

Alizadeh, Abdolali; Rezaiyehraad, Reza

doi:10.1007/s10593-021-02899-2

Cited by 5 publications

(2 citation statements)

References 29 publications

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“…The Tebby intermediate, formed in situ via the reaction between Ph 3 P and the dialkyl acetylenedicarboxylate, attacked the 3-cyanochromone and the resulting salt was transformed into the final product after proton migration, intramolecular cyclization, and a ring-opening reaction. 30…”

Section: Scheme 24 Synthesis Of (1-benzo[d]thiazol-2-ylimidazolidin-4...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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Section: Scheme 24 Synthesis Of (1-benzo[d]thiazol-2-ylimidazolidin-4...mentioning

confidence: 99%

Acetylenic Esters in Organic Synthesis

Hajinasiri¹

2022

Synlett

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“…[44] In 2021, Alizadeh and co-workers developed the threecomponent reaction of phosphonium salts 15, dialkyl acetylene dicarboxylate 1 and 3-cyanochromones 59 in dry CH 2 Cl 2 at room temperature for the synthesis of highly substituted zwitterionic furans 60 (Scheme 23). [45]…”

Section: Furansmentioning

confidence: 99%

Use of Dialkyl Acetylenedicarboxylates in the Multicomponent Synthesis of Heterocyclic Structures

2022

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Dialkyl acetylenedicarboxylates (DAAD) are the class of acetylenic compounds that are broadly used in organic synthesis in a noticeable quantity. Their wide application has made them an important moiety in heterocyclic compounds and drug discovery programs. Dialkyl acetylenedicarboxylate is a di-ester in which the ester groups are conjugated with a carbon-carbon triple bond. As such, the molecule is very electrophilic, and is broadly used as a dienophile in various cycloaddition reactions, for example the Diels-Alder reaction. In addition, it is a strong Michael acceptor. Due the importance of dialkyl acetylenedicarboxylate in organic synthesis, we are trying to show the applications of this compound in the synthesis of different heterocycles using multicomponent reactions. In this review, we show recent advances (2016)(2017)(2018)(2019)(2020)(2021)(2022) for the synthesis of various heterocycles that have different ring sizes (five, six and seven membered, Spiro and fused heterocycles), using DAAD via multicomponent reactions.

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Efficient, Concise, and Chemoselective Synthesis of 1H‐Benzo[f]indole‐4,9‐dione with 4‐Hydroxycoumarin Substituent via a One‐Pot Three‐Component Reaction

Alizadeh,

Hasanpour,

Rezaiyehraad

2023

ChemistrySelect

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Extensive studies on the biological activities of several quinone‐fused heterocycles have confirmed their outstanding antitumor activity. Therefore, a new family of 1H‐benzo[f]indole‐4,9‐dione derivatives with the 4‐hydroxycoumarin substitution was prepared by a high‐yield, one‐pot, concise three‐component reaction between arylglyoxals, 4‐hydroxycoumarin, and 2‐aminonaphthalene‐1,4‐dione derivatives under reflux in EtOH. This efficient protocol showed chemoselectivity in addition to facile operation procedure and easy purification.

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Group-assisted purification chemistry principles to access highly substituted zwitterionic furans via fast, concise, and efficient one-pot three-component assembly

Cited by 5 publications

References 29 publications

Acetylenic Esters in Organic Synthesis

Acetylenic Esters in Organic Synthesis

Use of Dialkyl Acetylenedicarboxylates in the Multicomponent Synthesis of Heterocyclic Structures

Efficient, Concise, and Chemoselective Synthesis of 1H‐Benzo[f]indole‐4,9‐dione with 4‐Hydroxycoumarin Substituent via a One‐Pot Three‐Component Reaction

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