Synthesis of Naphthalene Derivatives from <i>ortho</i>-Alkynylacetophenone Derivatives via Tandem <i>in Situ</i> Incorporation of Acetal and Intramolecular Heteroalkyne Metathesis/Annulation

Manojveer, Seetharaman; Balamurugan, Rengarajan

doi:10.1021/ol5003835

Cited by 49 publications

(15 citation statements)

References 61 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The undesired results were obtained possibly because TfOH is not compatible with these water scavengers. 4 Å MS may capture TfOH due to its basic characters, while HC(OMe) 3 reacted quickly with ketones to yield a mixture including methyl vinyl ether and dimethyl ketals …”

Section: Results and Discussionmentioning

confidence: 99%

Tandem Synthesis of 1,3-Disubstituted Naphthalenes via TfOH-Promoted Directed-Aldol and Friedel–Crafts Reactions

Shan

Lin

et al. 2021

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

Section: Results and Discussionmentioning

confidence: 99%

Tandem Synthesis of 1,3-Disubstituted Naphthalenes via TfOH-Promoted Directed-Aldol and Friedel–Crafts Reactions

Shan

Lin

et al. 2021

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…Balamurugan et al [79] . also established a concise approach to synthesizing naphthalene derivatives from readily available accessible o‐alkynylacetophenones with the aid of TfOH catalyst (Scheme 49).…”

Section: Neutral Additives‐induced Reactionsmentioning

confidence: 99%

“…Balamurugan et al [79] also established a concise approach to synthesizing naphthalene derivatives from readily available accessible o-alkynylacetophenones with the aid of TfOH catalyst (Scheme 49). In this system, an orthoformate, HC (OMe) 3 , was also used, and intriguingly, it was used as dual additive and substrate in this reaction.…”

Section: Orthoformatesmentioning

confidence: 99%

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

Chen

Bai

et al. 2020

The Chemical Record

View full text Add to dashboard Cite

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.

show abstract

“…Consequently, a number of synthetic strategies toward polysubstituted naphthalenes or phenanthrenes have been developed. The most important avenues include the Diels–Alder reaction, annulation reaction, metathesis, rearrangements of strained rings, catalytic cyclization, C–H activation, cycloisomerization, and cross-coupling protocols . In addition, N-heteroarenes such as quinolines and benzocarbazoles also feature prominently among many natural products and drug candidates .…”

Section: Introductionmentioning

confidence: 99%

Cu(I)-Catalyzed Ligand-Free Tandem One-Pot or Sequential Annulation via Knoevenagel Intermediates: An Entry into Multifunctional Naphthalenes, Phenanthrenes, Quinolines, and Benzo[b]carbazoles

2019

View full text Add to dashboard Cite

A simple but efficient one-pot or sequential copper-catalyzed protocol using 2-bromoaldehydes and active methylene group containing substrates that affords multifunctional naphthalenes, phenanthrenes, quinolines, and benzo[b]carbazoles via Knoevenagel condensation, C-arylation, and decarboxylation, followed by aromatization, is developed. The reaction utilizes the potential of Knoevenagel intermediates and does not require any ancillary ligand. The phenanthrene products thus obtained show moderate fluorescence activity. Structural elaboration of the products to obtain dihydrobenzoquinazolines is also highlighted.

show abstract

Synthesis of Naphthalene Derivatives from ortho-Alkynylacetophenone Derivatives via Tandem in Situ Incorporation of Acetal and Intramolecular Heteroalkyne Metathesis/Annulation

Cited by 49 publications

References 61 publications

Tandem Synthesis of 1,3-Disubstituted Naphthalenes via TfOH-Promoted Directed-Aldol and Friedel–Crafts Reactions

Tandem Synthesis of 1,3-Disubstituted Naphthalenes via TfOH-Promoted Directed-Aldol and Friedel–Crafts Reactions

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

Cu(I)-Catalyzed Ligand-Free Tandem One-Pot or Sequential Annulation via Knoevenagel Intermediates: An Entry into Multifunctional Naphthalenes, Phenanthrenes, Quinolines, and Benzo[b]carbazoles

Contact Info

Product

Resources

About