A Parham cyclization approach to diaryl-fused seven-membered ring heterocyclic ketones

Farrokh, John; Campos, Catherine A.; Hunt, David A.

doi:10.1016/j.tetlet.2015.07.043

Cited by 8 publications

(4 citation statements)

References 5 publications

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Section: Resultsmentioning

confidence: 99%

“…A Grignard-induced cyclization afforded ketone 2 in 73% yield from the Weinreb amide, while ketone 1 was obtained in 45% using n-BuLi to promote a Parham-type cyclization onto the nitrile. 13 We next sought to synthesize O-ABC and O-ABC-II from the synthesized precursor ketones (Scheme 1). 11b,12a-c Nucleophilic addition of N-morpholinomethyl-5-lithiotetrazole, followed by acid hydrolysis gave intermediate tetrazoles 1′ and 2′ in good yields (>60% over two steps).…”

Section: Cyclooctyne Synthesismentioning

confidence: 99%

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Oxa-azabenzobenzocyclooctynes (O-ABCs): heterobiarylcyclooctynes bearing an endocyclic heteroatom

Das,

Feliciano,

Yamanushkin

et al. 2023

Org. Biomol. Chem.

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Section: Resultsmentioning

confidence: 99%

Section: Cyclooctyne Synthesismentioning

confidence: 99%

Oxa-azabenzobenzocyclooctynes (O-ABCs): heterobiarylcyclooctynes bearing an endocyclic heteroatom

Das,

Feliciano,

Yamanushkin

et al. 2023

Org. Biomol. Chem.

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“…This strategy involves the generation of functionalized aryllithiums by bromine-lithium exchange, followed by intramolecular cyclization onto an electrophilic nitrile functional group. 20 Doxepin is a dibenzo[b,e]oxepine tricyclic with a tertiary amine chemical structure, which is marketed as a mixture of geometric isomers in a ratio of Z:E =15:85. It acts by inhibiting the reuptake of serotonin and norepinephrine at chemical synapses.…”

Section: A R T I C L E I N F Omentioning

confidence: 99%

Iron(II) promoted direct synthesis of dibenzo[b,e]oxepin-11(6H)-one derivatives with biological activity. A short synthesis of doxepin

et al. 2017

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A novel and efficient synthesis of dibenzo[b,e]oxepin-11(6H)-ones by direct intramolecular ortho-acylation from readily available 2-(phenoxymethyl)benzoic acids was developed. The method takes advantage of a newly developed cooperative system consisting of sustainable FeCl2 and Cl2CHOCH3 as the key components. This methodology is compatible with a wide variety of functional groups in good to excellent yields and high regioselectivity. The synthetic application of new protocol was extended to the synthesis of known tricyclic drug doxepin as well as a small library of oxepin based derivatives. For the first time, the obtained dibenzo[b,e]oxepinone derivatives were evaluated for their biological activities on the freeliving nematode Caenorhabditis elegans as an effective and cost-efficient model system for anthelmintic discovery.

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“…More recently, a new Parham cyclization methodology has been developed for the preparation of dibenzo [b,e]oxepinones. This strategy involves the generation of functionalized aryllithiums by bromine-lithium exchange, followed by intramolecular cyclization onto an electrophilic nitrile functional group [20].…”

mentioning

confidence: 99%

<strong>Efficient synthesis and biological evaluation of dibenzo[b,e]oxepin-11(6H)-ones as potential anthelmintic agents</strong>

Gerbino

Scoccia

Castro

et al. 2016

Proceedings of the 20th International Electronic Conference on Synthetic Organic Chemistry

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The first systematic study for the construction of a small library dibenzo[b,e]oxepin-11(6H)-ones by direct intramolecular acylation from readily available 2-(phenoxymethyl)benzoic acids was developed. For this purpose, a novel and efficient cooperative system consisting of SnCl2 and Cl2CHOCH3 is presented. This methodology show be compatible with a wide variety of functional groups in good to excellent yields and high regioselectivity. The generality of new protocol was applied to the scalable and reproducible synthesis of tricyclic antidepressant doxepin. The synthesized dibenzo[b,e]oxepins were evaluated for their biological activities using free-living nematode Caenorhabditis elegans as effective and cost-efficient model system for anthelmintic discovery.

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A Parham cyclization approach to diaryl-fused seven-membered ring heterocyclic ketones

Cited by 8 publications

References 5 publications

Oxa-azabenzobenzocyclooctynes (O-ABCs): heterobiarylcyclooctynes bearing an endocyclic heteroatom

Oxa-azabenzobenzocyclooctynes (O-ABCs): heterobiarylcyclooctynes bearing an endocyclic heteroatom

Iron(II) promoted direct synthesis of dibenzo[b,e]oxepin-11(6H)-one derivatives with biological activity. A short synthesis of doxepin

<strong>Efficient synthesis and biological evaluation of dibenzo[b,e]oxepin-11(6H)-ones as potential anthelmintic agents</strong>

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