Microwave-promoted efficient synthesis of spiroindenotetrahydropyridine derivatives via a catalyst- and solvent-free pseudo one-pot five-component tandem Knoevenagel/aza-Diels–Alder reaction

Bhuyan, Debajyoti; Sarmah, Manas M.; Dommaraju, Yuvaraj; Prajapati, Dipak

doi:10.1016/j.tetlet.2014.07.086

Cited by 26 publications

(5 citation statements)

References 38 publications

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“…According to the proposal of the authors, compound 138 may react with chalcone 1 through a Michael addition, leading to cyclization with ammonium acetate and the aldehyde to give pyridine 143 . Nevertheless, this idea was not investigated [152] . Prajapadi et al .…”

Section: Chalcones In Diels‐alder Cycloadditionsmentioning

confidence: 99%

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Chalcones, a Privileged Scaffold: Highly Versatile Molecules in [4+2] Cycloadditions

Mastachi-Loza

Ramírez-Candelero²,

Benítez‐Puebla

et al. 2022

Chemistry An Asian Journal

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Chalcones are aromatic ketones found in nature as the central core of many biological compounds. They have a wide range of biological activity and are biogenetic precursors of other important molecules such as flavonoids. Their pharmacological relevance makes them a privileged scaffold, advantageous for seeking alternative therapies in medicinal chemistry. Due to their structural diversity and ease of synthesis, they are often employed as building blocks for chemical transformations. Chalcones have a carbonyl conjugated system with two electrophilic centers that are commonly used for nucleophilic additions, as described in numerous articles. They can also participate in Diels-Alder reactions, which are [4 + 2] cycloadditions between a diene and a dienophile. This microreview presents a chronological survey of studies on chalcones as dienes and dienophiles in Diels-Alder cycloadditions. Although these reactions occur in nature, isolation of chalcones from plants yields very small quantities. Contrarily, synthesis leads to large quantities at a low cost. Hence, novel methodologies have been developed for [4 + 2] cycloadditions, with chalcones serving as a 2π or 4π electron system.

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Section: Chalcones In Diels‐alder Cycloadditionsmentioning

confidence: 99%

“…Nevertheless, this idea was not investigated. [152] Prajapadi et al explored different solvents, but found none to be the best condition for the transformation. Indeed, most of the solvents showed no reaction.…”

Section: Chalcones As Dienesmentioning

confidence: 99%

Chalcones, a Privileged Scaffold: Highly Versatile Molecules in [4+2] Cycloadditions

Mastachi-Loza

Ramírez-Candelero²,

Benítez‐Puebla

et al. 2022

Chemistry An Asian Journal

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“…Condensation of 93 with ammonium acetate followed by aza-Diels-Alder cycloaddition of dienophiles 93 affords products 92. Prajapati and co-workers reported a microwave reaction using two equiv each of 1,3indanediones and aromatic aldehydes and one equiv of ammonium acetate for the synthesis of novel spiroindenotetrahydropyridine derivatives 92 under catalyst-and solvent-free conditions involving cascade Knoevenagel/aza-Diels-Alder reactions (Scheme 39) [53]. The Knoevenagel condensation of indanedione and aldehydes gives dienophiles 93.…”

Section: Scheme 32 6c5cr For Bis(2-phenyl-23-dihydroquinazolin-4(1h)-ones)mentioning

confidence: 99%

“…thesis of novel spiroindenotetrahydropyridine derivatives 92 under catalyst-and solventfree conditions involving cascade Knoevenagel/aza-Diels-Alder reactions (Scheme 39) [53]. The Knoevenagel condensation of indanedione and aldehydes gives dienophiles 93.…”

Section: Scheme 32 6c5cr For Bis(2-phenyl-23-dihydroquinazolin-4(1h)-ones)mentioning

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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“…The Prajapati group, in 2014, developed a MW assisted neat reaction for the formation of complex spiroindenopyridine scaffolds. 216 During the initial study, they carried out the reaction by taking 2 mmol of p-fluorobenzaldehyde (249), 2 mmol of 1,3-indanedione (415) with 1.2 mmol of ammonium acetate (NH 4 OAc) under MW irradiation at 700 W for 7 min and obtained 85% yield of the spiropyridine derivative (416) (Scheme 118).…”

Section: Synthesis Of Spirooxindoles: Tandem Knoevenagel/michael Addi...mentioning

confidence: 99%

A decade update on solvent and catalyst-free neat organic reactions: a step forward towards sustainability

Sarkar

Santra

Kundu³

et al. 2016

Green Chem.

204

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The keen success has been achieved towards the synthesis of new product and process as the twelve principle of "Green Chemistry" was formulated in 1990s. These products and processes are more compatible with human health, society and the environment. In this review a collection of researches has been documented from the view point of green chemistry. The main theme of this review is neat reactions which are solvent and catalyst-free reactions. Neat reactions in absence of any solvents and catalysts with the concise forms of microwaves, ball milling neat reactions have been described.

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Microwave-promoted efficient synthesis of spiroindenotetrahydropyridine derivatives via a catalyst- and solvent-free pseudo one-pot five-component tandem Knoevenagel/aza-Diels–Alder reaction

Cited by 26 publications

References 38 publications

Chalcones, a Privileged Scaffold: Highly Versatile Molecules in [4+2] Cycloadditions

Chalcones, a Privileged Scaffold: Highly Versatile Molecules in [4+2] Cycloadditions

Recent Developments on Five-Component Reactions

A decade update on solvent and catalyst-free neat organic reactions: a step forward towards sustainability

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