Intramolecular [4 + 2] Cycloaddition Reactions of Diarylacetylenes:  Synthesis of Benzo[b]fluorene Derivatives via Cyclic Allenes

Rodrı́guez, David; Navarro, Armando; Castedo, Luís; Domı́nguez, Domingo; Saá, Carlos

doi:10.1021/ol991391t

Cited by 92 publications

(48 citation statements)

References 27 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Aryl amines (78) forms Pd II chelate complex that leads to a five-membered complex (79). Oxidative addition took place to form Pd IV complex (80) and reductive addition furnished ortho arylated product 81.…”

Section: Intermolecular Synthesis Of Fluorenonesmentioning

confidence: 99%

“…Benzodiynone (190) underwent thermal cycloaddition in toluene at 150°C for 11 h lead to 191 and 192 in 72 % and 24 % of fluorenone (Scheme 66). [78] Recently, Hoye et al reported a new protocol for the synthesis of substituted fluorenones via benzyne cascade reaction. Thermal isomerization of tri-yne benzyne (193) via hexadehydro-Diels-Alder (HDDA) reaction led to substituted fluorenones in moderate to good yields (Scheme 67).…”

Section: Intramolecular Synthesis Of Fluorenonesmentioning

confidence: 99%

See 1 more Smart Citation

A Perspective on Synthesis and Applications of Fluorenones

et al. 2020

View full text Add to dashboard Cite

Fluorenones are important constituents in material, medical and chemical sciences with potential applications in various domains. The key factors responsible for the diverse usage of fluorenones in material sciences are their intriguing and tunable photo, as well as physico‐chemical properties. Besides this, the presence of conjugated poly‐(en)ynes in the fluorenones makes them molecules of interest in material sciences. Fluorenones show various biological activities like antibiotics, anticancer, antiviral, and neuromodulatory, etc. Organic chemists are developing various protocols for the synthesis of fluorenones. Despite several protocols developed for their synthesis since 1931, there is no review covering their entire synthetic protocols. This review includes several classical and novel synthetic approaches for the synthesis of fluorenones. Furthermore, we delineated the mechanism by which they have been synthesized.

show abstract

Section: Intermolecular Synthesis Of Fluorenonesmentioning

confidence: 99%

Section: Intramolecular Synthesis Of Fluorenonesmentioning

confidence: 99%

A Perspective on Synthesis and Applications of Fluorenones

et al. 2020

View full text Add to dashboard Cite

show abstract

“…Another approach by Mal et al was based on ring contraction via the benzil-benzilic acid rearrangement of benzo[a]anthracene-5,6-diones [16]. Other noteworthy approaches are those utilizing [4+2] cycloadditions [17,18], other cycloadditions [17,19,20], and oxidative free radical cyclizations [21]. Birman and co-workers achieved the rapid ring construction of benzo[b]fluorenones via reaction of 1-indanone dianions with phthalate diesters.…”

Section: Introductionmentioning

confidence: 99%

A new approach towards synthesis of benzo[b]fluorene core

Bogdanov

2014

Maced. J. Chem. Chem. Eng.

View full text Add to dashboard Cite

New approach towards synthesis of benzo[b]fluorene core is described. The model compound, 10-methoxy-11H-benzo[b]fluoren-11-one was prepared in five steps starting from dibenzylmalonic acid. The key step was the metal catalyzed rearrangement of 3,3’-dihalo-2,2’-spirobiindan-1,1’-dione. The choice and proper activation of the metal was critical for the assembly of the benzo[b]fluorenone system. The zinc mediated rearrangement of the corresponding dibromo derivative led to the 10-hydroxy-11H-benzo[b]fluoren-11-one derivative in 52% yield. The structure of the product was established by spectroscopic methods and was additionally confirmed by standard methylation reaction to the 10-methoxy derivative, which is known in the literature.

show abstract

“…[27] Saá and co-workers have extensively studied similar arylalkyne-alkyne cycloadditions. [28,29] In this paper, we report full details of our work, directed towards the synthesis of kinamycins based on the intramolecular reaction of arylalkynes with allenes or alkynes.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of the Benzo[b]fluorene Core of the Kinamycins by Arylalkyne–Allene and Arylalkyne–Alkyne Cycloadditions

et al. 2006

View full text Add to dashboard Cite

Arylalkyne–allene and arylalkyne–alkyne cycloadditions yields benzo[a]fluorenones, which are related to the tetracyclic core of the kinamycins. In the arylalkyne–alkyne cycloadditions, we found a rearrangement that produces benzo[a]fluorenones, in addition to the expected benzo[b]fluorenones. This rearrangement could be suppressed in the presence of phenol, which allowed the synthesis of 4,9‐dimethoxy‐2‐methyl‐11H‐benzo[b]fluoren‐11‐one in excellent yield.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

show abstract

Intramolecular [4 + 2] Cycloaddition Reactions of Diarylacetylenes: Synthesis of Benzo[b]fluorene Derivatives via Cyclic Allenes

Cited by 92 publications

References 27 publications

A Perspective on Synthesis and Applications of Fluorenones

A Perspective on Synthesis and Applications of Fluorenones

A new approach towards synthesis of benzo[b]fluorene core

Synthesis of the Benzo[b]fluorene Core of the Kinamycins by Arylalkyne–Allene and Arylalkyne–Alkyne Cycloadditions

Contact Info

Product

Resources

About