<i>In Situ</i> Formed Acetal-Facilitated Synthesis of Substituted Indene Derivatives from <i>o</i>-Alkenylbenzaldehydes

Manojveer, Seetharaman; Balamurugan, Rengarajan

doi:10.1021/acs.orglett.5b01695

Cited by 25 publications

(7 citation statements)

References 75 publications

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“…Proceeding on the same line, Balamurugan et al [81] . also established a fast and expedient in situ generated acetal‐promoted protocol for diastereoselective synthesis of indene derivatives (Scheme 51).…”

Section: Neutral Additives‐induced Reactionsmentioning

confidence: 99%

“…Subsequently, I161 might undergo two different pathways to afford naphthalene product 135, and the intervention of HC(OMe) 3 might also be involved in the late stage. Proceeding on the same line, Balamurugan et al [81] also established a fast and expedient in situ generated acetalpromoted protocol for diastereoselective synthesis of indene derivatives (Scheme 51). The orthoformate additive, HC Control experiments shown that a compound 139 can be converted readily into 140 in the absence of HC(OMe) 3 with the aid of TfOH catalyst.…”

Section: Orthoformatesmentioning

confidence: 99%

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Acid‐Acid‐Catalyzed Tandem Reactions Driven by an Additive‐Like Component

Chen

Bai

et al. 2020

The Chemical Record

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Acid‐catalyzed tandem reactions with auto‐tandem catalysis are effective for simplifying organic synthesis. However, some of the reported reactions were established based on the use of well‐designed substrate with complex structure. In some cases, owing to the existence of a big gap between each catalytic cycle, it is hard to bind all the individual reaction steps to be a peaceful sequence. To enrich the diversity and also to strengthen the practical usefulness of the methodology developed by auto‐tandem catalysis, an additive‐like component was added to induce acid‐acid‐catalyzed tandem reaction. During the reaction, the additive‐like component acted either as an activator to increase the reactivity of the starting material or a hided reagent to enable successful transformation of the intermediate. Many novel tandem reactions were established in a one‐pot manner with the aid of this strategy. Importantly, this strategy not only allows the use of simple and commercially available chemicals as substrates, but also possesses multiple merits, such as simplifying operation, lowering waste generation and enhancing synthetic efficiency and atom‐economy. A summarization of the additive‐like component‐induced auto‐tandem catalysis with an acid catalyst was given in this review, in which many acid‐acid‐catalyzed tandem reactions were discussed. The reported additive‐like components were classified as three types: oxidative type, reductive type and neutral type depending on their mechanisms in assisting the establishment of acid‐acid‐catalyzed tandem reactions. Many examples were collected and analyzed from the viewpoints of simplifying the synthesis and manifesting their superior and distinct functionalities of the additives. A perspective of this concept was also given at the end of this review.

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Section: Neutral Additives‐induced Reactionsmentioning

confidence: 99%

Section: Orthoformatesmentioning

confidence: 99%

Acid‐Acid‐Catalyzed Tandem Reactions Driven by an Additive‐Like Component

Chen

Bai

et al. 2020

The Chemical Record

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“…In the experiment, fully deuterated trimethyl orthoformate (DC(OCD 3 ) 3 ) was used in place of trimethyl orthoformate under the optimized conditions that showed deuterium incorporation at C2 of the 1-acylnaphthalene 583 . 102…”

Section: Lewis Acid Catalyzed Reactionsmentioning

confidence: 99%

Chemical Synthesis of Substituted Naphthalene Derivatives: A Review

Hussain,

Maheshwari

2023

Synthesis

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This review article outlines the progress made in the synthesis of substituted naphthalene derivatives. Naphthalene and its derivatives exhibit various biological activities such as anti-inflammatory, anticancer, antiviral, antitubercular, antimicrobial, antihypertensive, antidiabetic, etc. Several strategies have been developed in the past for the construction of naphthalene derivatives, primarily focused on Metal-catalyzed reactions (palladium, copper, zinc, rhodium, platinum, nickel, etc.,) and Lewis acid-catalyzed transformations. This review discusses the preparations of naphthalene derivatives using various salt such as gallium chlorides, gold chlorides, gold bromides, various gold complexes as well as bronsted acids like triflic acid and trifluoroacetic acid, and Lewis acids such as like boron trifluoride etherate. Additionally, miscellaneous reactions involving metal and Lewis acids are explored. The transformational approaches covered in this review include cycloadditions, carboannulations, benzoannulations, electroannulations, rearrangements, and cross-dehydrogenative coupling reactions. Overall this review provides a comprehensive and up-to-date account of the current state of preparations of substituted naphthalenes, highlighting their medicinal and industrial importance.

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“…Iodine-promoted and base-promoted cyclization reactions have been reported. Lewis and Brønsted acid-catalyzed reactions of alkene conjugate addition have been studied . It is desirable to find new efficient methods to construct variously functionalized indene derivatives.…”

Section: Introductionmentioning

confidence: 99%

Sequential Knoevenagel Condensation/Cyclization for the Synthesis of Indene and Benzofulvene Derivatives

et al. 2021

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Sequential Knoevenagel condensation/cyclization leading to indene and benzofulvene derivatives has been developed. The reaction of 2-(1-phenylvinyl)benzaldehyde with malonates gave benzylidene malonates, cyclized indenes, and dehydrogenated benzofulvenes. The product selectivity depends on the reaction conditions. The reaction with piperidine, AcOH in benzene at 80 °C for 1.5 h gave a benzylidene malonate in 75% yield as a major product. The reactions with piperidine, AcOH in benzene at 80 °C for 17 h and with TiCl 4 -pyridine at room temperature gave an indene derivative in 56 and 79% yields, respectively, as a major product. The reaction with TiCl 4 -Et 3 N gave a benzofulvene in 40% yield selectively. Indene was transformed to a benzofulvene derivative using the reagents TiCl 4 -Et 3 N and 2,3-dichloro-5,6dicyano-1,4-benzoquinone (DDQ). The reaction of variously substituted aryl derivatives with dimethyl malonate gave indene and benzofulvene derivatives. The reactions of 2-(1-phenylvinyl)benzaldehyde with Meldrum's acid or malononitrile also gave cyclized compounds in the suitable sequential or stepwise conditions. Furthermore, the reaction of 2-arylbenzaldehydes has been investigated. The limitation and scope have been described. The reaction mechanism of the cyclization steps has been examined by DFT calculations.

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In Situ Formed Acetal-Facilitated Synthesis of Substituted Indene Derivatives from o-Alkenylbenzaldehydes

Cited by 25 publications

References 75 publications

Acid‐Acid‐Catalyzed Tandem Reactions Driven by an Additive‐Like Component

Acid‐Acid‐Catalyzed Tandem Reactions Driven by an Additive‐Like Component

Chemical Synthesis of Substituted Naphthalene Derivatives: A Review

Sequential Knoevenagel Condensation/Cyclization for the Synthesis of Indene and Benzofulvene Derivatives

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