An Efficient Five‐Component Reaction for the Synthesis of 4,4′‐((2‐Oxoindoline‐3,3‐diyl)bis(methylene))bis(2‐aryl‐1H‐pyrrolo[3,4‐c]quinoline‐1,3(2H)‐dione) Derivatives

Mao, Kaimin; Dai, Lei; Liu, Yun; Rong, Liangce

doi:10.1002/jhet.3592

Cited by 7 publications

(4 citation statements)

References 43 publications

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“…[48] There are few cascade reactions in which two or three molecules of the starting materials are utilised in the process to arrive at the final product. One such example was reported by Mao et al [49] where three equivalences of isatin 1 and two equivalences of 1,3-dicarbonyl compounds 69 react in the presence of hydrated p-toluene sulfonic acid (p-TSA) to construct derivatives of pyrrolo-quinolines 72 with more straightforward workup procedures (Scheme 14). The reaction mechanism involves nucleophilic addition, Knoevenagel condensation, intramolecular annulation, and cyclisation (Scheme 15).…”

Section: Tripartite Domino Synthesis Of Quinolines and Their Derivativesmentioning

confidence: 99%

Single Step Upgradation of Isatin to Bioactive Fused Heterocycles via Ring Expansion Reactions

Chandramani,

Nair,

Sreekumar

et al. 2023

Eur J Org Chem

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Isatin, also known as indoline‐2,3‐dione, is a fused, N‐heterocyclic aromatic compound first isolated and purified in 1841. Since then, isatin and its derivatives emerged as a hot research topic for the scientific community. The number of research publications on isatin justifies their popularity. Researchers explored isatins and their derivatives as potential candidates in multidisciplinary research areas, including medicinal chemistry, synthetic organic chemistry, and polymer science. Synthetic chemists’ perspective of tailoring isatin and its family members led to more efficient synthesis strategies in which ring‐opening reactions of isatins were particularly significant due to the product's importance. Our investigation aims to group the different types of cascade ring expansion reactions of isatin to synthesise fused heterocyclic compounds such as derivatives of quinolines, quinazolinones, acridines, acridones, and few spiro heterocyclic compounds, all of which highlight an inevitable role in the field of medicinal chemistry.

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Section: Tripartite Domino Synthesis Of Quinolines and Their Derivativesmentioning

confidence: 99%

Single Step Upgradation of Isatin to Bioactive Fused Heterocycles via Ring Expansion Reactions

Chandramani,

Nair,

Sreekumar

et al. 2023

Eur J Org Chem

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“…These scaffolds were obtained by reacting different isatins (3 equivalents) with acetoacetyl aromatic amines (2 equivalents) in the presence of p ‐toluenesulfonic acid, under mild conditions, to give the products in very good yields (Scheme 127). [253] …”

Section: Other Oxindole Derivativesmentioning

confidence: 99%

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

Brandão

Marques

Carreiro

et al. 2021

The Chemical Record

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Multicomponent reactions (MCRs) are a valuable tool in diversity‐oriented synthesis. Its application to privileged structures is gaining relevance in the fields of organic and medicinal chemistry. Isatin, due to its unique reactivity, can undergo different MCRs, affording multiple interesting scaffolds, namely oxindole‐derivatives (including spirooxindoles, bis‐oxindoles and 3,3‐disubstituted oxindoles) and even, under certain conditions, ring‐opening reactions occur that leads to other heterocyclic compounds. Over the past few years, new methodologies have been described for the application of this important and easily available starting material in MCRs. In this review, we explore these novelties, displaying them according to the structure of the final products obtained.

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“…Reactions of three molecules of A with two molecules of B is a very special MCR process. Rong and co-workers developed a reaction involving three equiv of isatins and two equiv of 3-oxo- N -arylbutanamide for the synthesis of pyrrolo[3,4- c ]quinoline derivatives 126 ( Scheme 52 ) [ 72 ]. In the reaction process, isatins first react with two molecules of acetoacetanilides followed by the Knoevenagel condensation reaction with two molecules of isatins to form intermediates 127 .…”

Section: Type-v Pseudo-5crs Of 3a + 2bmentioning

confidence: 99%

“…A schematic of a Type-V pseudo-5CRs involving 3A + Reactions of three molecules of A with two molecules of B is Rong and co-workers developed a reaction involving three e of 3-oxo-N-arylbutanamide for the synthesis of pyrrolo[3,4 (Scheme 52) [72]. In the reaction process, isatins first react w acetanilides followed by the Knoevenagel condensation rea isatins to form intermediates 127.…”

Section: Type-v Pseudo-5crs Of 3a + 2bmentioning

confidence: 99%

Recent Developments on Five-Component Reactions

Zhi

Zhang

2021

Molecules

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Multicomponent reactions (MCRs) have inherent advantages in pot, atom, and step economy (PASE). This important green synthetic approach has gained increasing attention due to high efficiency, minimal waste, saving resources, and straightforward procedures. Presented in this review article are the recent development on 5-compoment reactions (5CRs) of the following six types: (I) five different molecules A + B + C + D + E; pseudo-5CRs including (II) 2A + B + C + D, (III) 2A + 2B + C, (IV) 3A + B + C, (V) 3A + 2B, and (VI) 4A + B. 5CRs with more than five-reaction centers are also included.

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An Efficient Five‐Component Reaction for the Synthesis of 4,4′‐((2‐Oxoindoline‐3,3‐diyl)bis(methylene))bis(2‐aryl‐1H‐pyrrolo[3,4‐c]quinoline‐1,3(2H)‐dione) Derivatives

Cited by 7 publications

References 43 publications

Single Step Upgradation of Isatin to Bioactive Fused Heterocycles via Ring Expansion Reactions

Single Step Upgradation of Isatin to Bioactive Fused Heterocycles via Ring Expansion Reactions

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

Recent Developments on Five-Component Reactions

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