Diastereoselective One-Pot Synthesis of Succinimides Bearing a Chromone Unit

Teimouri, Mohammad Bagher; Asnaashari, Bita; Moayedi, Maryam; Naderi, Soheila

doi:10.1055/s-0034-1378926

Cited by 9 publications

(4 citation statements)

References 12 publications

(19 reference statements)

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“…Furthermore, in 2015, a very interesting variant of the above-reviewed protocol was reported by Teimouri et al Biologically relevant chromone-bound succinimides 60 were synthesized through a four-component tandem reaction of 3formylchromones with Meldrum's acid, alkyl isocyanides and alcohols (Scheme 34). [71] The products were obtained with high diastereoselectivity under catalyst-free conditions in dry dichloromethane solvent. The merit of this diastereoselective cascade reaction is highlighted by its mild reaction conditions, easy work-up, acceptable yields, high bond efficiency, and two stereocenters in a single operation.…”

Section: Miscellaneous Imcrs For the Synthesis Of Bound Type Bhcsmentioning

confidence: 97%

One‐Pot Construction of Bis‐Heterocycles through Isocyanide Based Multicomponent Reactions

Bhat

2020

ChemistrySelect

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Bis‐heterocycles (BHCs) are hybrid molecules comprising two linked, bound, spacer, or fused heterocyclic skeletons. In recent years, these compounds have attracted increased attention of scientific communities because of their improved potential applications than their discrete units. The emergence of numerous synthetic protocols utilizing Isocyanide as one of the components in multicomponent reactions has unleashed innumerable openings to design and synthesize diverse heterocyclic scaffolds and thus Isocyanide based multicomponent reactions (IMCRs) are leading today's MCR chemistry. To date, there has not been any exclusive review on the construction of BHCs via direct IMCRs or its combination with other reaction sequences in one‐pot. This article presents the first overview of IMCRs such as Ugi, Groebke‐Blackburn‐Bienaymé (GBBR), their sequential combination with other reactions, and new IMCRs established for the one‐pot synthesis of BHCs in the last two decades.

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Section: Miscellaneous Imcrs For the Synthesis Of Bound Type Bhcsmentioning

confidence: 97%

One‐Pot Construction of Bis‐Heterocycles through Isocyanide Based Multicomponent Reactions

Bhat

2020

ChemistrySelect

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“…42 Four-component condensation of 3-formylchromones 1, Meldrum´s acid, alkyl isocyanide, and alcohol resulted in succinimide derivatives 15 (Scheme 4). 43 The reaction proceeded at room temperature chemo-and regioselectively to give products 15 in reasonable yields.…”

Section: Isofl Avone Hetero Analogs With Fi Ve-membered Heterocyclesmentioning

confidence: 99%

“…This approach is tolerated to a wide variety of the substituents R 2 and R 3 , while the use of methanol promoted the pyrrolidone ring opening to give amido diesters 16 43 (see Scheme 4).…”

Section: Isofl Avone Hetero Analogs With Fi Ve-membered Heterocyclesmentioning

confidence: 99%

Synthesis of heterocyclic analogs of isoflavone and homoisoflavone based on 3-formylchromone

et al. 2021

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The review is focused on recent developments of chemistry of synthetic analogs of natural compounds, isofl avone and homoisofl avone. The possible synthetic strategies to access heterocyclic analogs of these compounds starting from readily available 3-formylchromone and its derivatives (3-cyanochromone, 2-amino-3-formylchromone) and products of its condensation with simplest Cand N-nucleophiles are discussed. The structural features of the reaction products that depend on the nature of the reaction medium, structure of the starting compounds, and reagent ratio are considered. Particular attention is given to the application of the modern strategies of organic synthesis, namely green chemistry approaches, click reactions, domino reactions, etc. Examples of compounds of this group most promising for clinical application due to wide and pronounced pharmacological eff ects are given.

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“…Recently, Teimouri et al. have described the multicomponent cascade reaction of 3‐formylchromones, isocyanides and methanol in CH 2 Cl 2 which provides polyfunctionalized succinimide derivatives after 24 h in moderate yields . In 2018, the same group has benefit of isocyanides and 3‐formylchromones‐based multicomponent reactions for the synthesis of the biological active compounds .…”

Section: Introductionmentioning

confidence: 99%

Choline Chloride/ Urea as Mild Media for the Synthesis of the Chromonyl Amidodiester Fragments and Succinimide Derivatives

et al. 2019

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A simple, green protocol has been accomplished for the synthesis of amidoesters 5 a-k in choline chloride/urea (1:2) through multicomponent reaction of 3-formyl chromone, Meldrum's acid, isocyanides and primary alcohols via a domino reaction. Carrying out the reaction using trifluoroethanol led to succinimide derivatives 6 a-d. Easy work-up, selectivity, and good to excellent yields are the advantages of this protocol.

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Diastereoselective One-Pot Synthesis of Succinimides Bearing a Chromone Unit

Abstract: A diastereoselective synthesis of highly substituted succinimide derivatives with chromone and carboxylic ester functionalities from 3-formylchromones, Meldrum's acid, and alkyl isocyanides in the presence of alcohols in moderate to good yields is described.

Cited by 9 publications

References 12 publications

One‐Pot Construction of Bis‐Heterocycles through Isocyanide Based Multicomponent Reactions

One‐Pot Construction of Bis‐Heterocycles through Isocyanide Based Multicomponent Reactions

Synthesis of heterocyclic analogs of isoflavone and homoisoflavone based on 3-formylchromone

Choline Chloride/ Urea as Mild Media for the Synthesis of the Chromonyl Amidodiester Fragments and Succinimide Derivatives

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