Synthesis of a Novel Serotonin-3 (5-HT<sub>3</sub>) Receptor Antagonist

Sugiura, Tsuneyuki; Matsui, Takuya; Nakai, Hisao; Okamoto, Masaki; Hashimoto, Shinsuke; Iguchi, Yoichi; Wakatsuka, H.; Kawamura, Masanori

doi:10.1055/s-1992-21405

Cited by 3 publications

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“…Tricyclic lactam compounds have been prepared using intramolecular cyclization, for example Friedel-Crafts reaction, 31 Bischler-Napieralski reaction 32,33 and lactam cyclization reaction. 34 We hypothesized that 4-bromobenzo[b]furans having the vinylcarbonylamino group (-NHCOCH=CH-R) at the 3-position would be subject to intramolecular cyclization between the two groups to form seven-membered lactam fused benzo[b]furan rings under Heck coupling conditions. 35 3-Amino-4-bromobenzo[b]furans (12), key intermediates to synthesize the tricyclicbenzo[b]furan (D), were prepared.…”

Section: Chemistrymentioning

confidence: 99%

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Synthesis and biological activities of novel furo[2,3,4-jk][2]benzazepin-4(3H)-one derivatives

et al. 2007

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A novel seven-membered lactam formation method has been established by intramolecular ring closure reaction of 4-bromo-(E)-3-[(2-alkylvinyl)carbonylamino]benzo[b]furans under Heck coupling conditions. A number of furo[2,3,4-jk][2]benzazepin-4(3H)-ones, tricyclicbenzo[b]furans, have been prepared by this method and evaluated for their leukotriene B(4) (LTB(4)) receptor and poly(ADP-ribose)polymerase-1 (PARP-1) inhibitory activities.

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Section: Chemistrymentioning

confidence: 99%

“…The solvent was evaporated off. The residue was recrystallized from ethyl acetate to give 20a (0.06 g, 34…”

Section: -Acetyl-7-methoxy-6-phenylfuro[234-jk][2]benzazepin-4(3h)one...mentioning

confidence: 99%

Synthesis and biological activities of novel furo[2,3,4-jk][2]benzazepin-4(3H)-one derivatives

et al. 2007

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Halogenation of Hydrocarbons

Larock

Zhang

2018

Comprehensive Organic Transformations

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Furan ring opening - isocoumarine ring closure: A recyclization reaction of 2-carboxyaryldifurylmethanes

Абаев

Dmitriev

Podelyakin

et al. 2006

Journal of Heterocyclic Chemistry

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A general method for the synthesis of isocoumarine derivatives has been developed. Bis(5‐R‐2‐furyl)methylbenzoic acids (R = methyl, ethyl) underwent recyclization and subsequent cyclization into tetracyclic isochromene‐1‐one derivatives under treatment with hydrogen chloride in methanol. It has been shown that intermediate 4‐(5‐R‐furan‐2‐yl)‐3‐(3‐oxo‐3‐R‐propyl)‐isochromene‐1‐ones can be obtained selectively by varying a concentration of the hydrogen chloride and reaction times. In the case of R = tert‐butyl only corresponding 4‐[5‐(tert‐butyl)‐2‐furyl]‐3‐(4,4‐dimethyl‐3‐oxopentyl)‐1‐isochromenones were isolated regardless of the reaction conditions.

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Synthesis of a Novel Serotonin-3 (5-HT₃) Receptor Antagonist

Cited by 3 publications

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Synthesis and biological activities of novel furo[2,3,4-jk][2]benzazepin-4(3H)-one derivatives

Synthesis and biological activities of novel furo[2,3,4-jk][2]benzazepin-4(3H)-one derivatives

Halogenation of Hydrocarbons

Furan ring opening - isocoumarine ring closure: A recyclization reaction of 2-carboxyaryldifurylmethanes

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Synthesis of a Novel Serotonin-3 (5-HT3) Receptor Antagonist

Cited by 3 publications

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Synthesis and biological activities of novel furo[2,3,4-jk][2]benzazepin-4(3H)-one derivatives

Synthesis and biological activities of novel furo[2,3,4-jk][2]benzazepin-4(3H)-one derivatives

Halogenation of Hydrocarbons

Furan ring opening - isocoumarine ring closure: A recyclization reaction of 2-carboxyaryldifurylmethanes

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Synthesis of a Novel Serotonin-3 (5-HT₃) Receptor Antagonist