One-Step Synthesis of Heteroaromatic-Fused Pyrrolidines via Cyclopropane Ring-Opening Reaction:  Application to the PKCβ Inhibitor JTT-010

Tanaka, Masahiro; Ubukata, M.; Matsuo, Takafumi; Yasue, Katsutaka; Matsumoto, Katsuya; Kajimoto, Yasuyuki; Ogo, Takashi; Inaba, Takashi

doi:10.1021/ol071336h

Cited by 90 publications

(24 citation statements)

References 26 publications

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“…A one‐step synthesis of 2,3‐dihydropyrrolo[1,2‐ a ]indoles 47 , 48 , and 49 based on addition of a furan‐cyclopropane reagent via the NC 2 bond of an indole ring was described . This method was successfully used in the synthesis of a new class of selective protein kinase inhibitors С‐β .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Some Biological Properties of Pyrrolo[1,2‐a]indoles

Monakhova

Ryabova

Makarov

2015

Journal of Heterocyclic Chem

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Section: Introductionmentioning

confidence: 99%

Synthesis and Some Biological Properties of Pyrrolo[1,2‐a]indoles

Monakhova

Ryabova

Makarov

2015

Journal of Heterocyclic Chem

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“…For the synthesis of 4a , a halide‐assisted ring opening followed by an intramolecular ring closing is developed as an alternative route (Scheme ) 1a. 14 When NaI was added into a chloroform solution of 2a at room temperature, the color of the solution changed from deep‐purple to green in one hour.…”

Section: Resultsmentioning

confidence: 99%

Reactions of Ruthenium–Allenylidene Complexes Tethering a Cyclopropyl Group

Chen

Cheng

Huang

et al. 2011

Chemistry An Asian Journal

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Two cyclopropyl allenylidene complexes [Ru]=C=C=C(R)(C(3)H(5)) ([Ru]=[RuCp(PPh(3))(2)], Cp=Cyclopentadienyl; R=thiophene (2a) and R=Ph (2b)) are prepared from the reactions of [Ru]Cl with the corresponding 1-cyclopropyl-2-propyn-1-ol in the presence of KPF(6). Thermal treatment, halide-anion addition, and palladium-catalyzed reactions of 2a and 2b all lead to a ring expansion of the cyclopropyl group, giving the vinylidene complexes 4a and 4b, respectively, each with a five-membered ring. This ring expansion proceeds by C-C bond formation between Cβ of the cumulative double bond and a methylene group of the cyclopropyl ring. In the reaction of 2a with pyrrole, consecutive formation of two C-C bonds, one between C-2 of pyrrole and Cγ of 2a and the other between C-3 of pyrrole and Cα, results in the formation of 6a. The reaction proceeds by addition of pyrrole and 1,3-proton shifts. The hydrogenation of 2a by NaBH(4) is carried out in different solvents. The cumulative double bonds are reduced regioselectively to give a mixture of 7a and 8a. Interestingly, use of different solvents leads to different ratios of 7a and 8a. Presence of a protic solvent like methanol in dichloromethane or chloroform solution increases the yield of 8a, thus revealing that both the rates of hydroboration and deboronation increase. The structures of two new complexes 4a and 6a have been firmly established by X-ray diffraction analysis.

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“…148 Analogous processes were carried out for imidazoles and benzimidazoles. Based upon this reaction, they devised a synthesis of the protein kinase C-β inhibitor JTT-010 (Scheme 94).…”

Section: Short Review Syn Thesismentioning

confidence: 99%

Ring Opening of Donor–Acceptor Cyclopropanes with N-Nucleophiles

et al. 2017

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Ring opening of donor-acceptor cyclopropanes with variousN-nucleophiles provides a simple approach to 1,3-functionalized compounds that are useful building blocks in organic synthesis, especially in assembling various N-heterocycles, including natural products. In this review, ring-opening reactions of donor-acceptor cyclopropanes with amines, amides, hydrazines, N-heterocycles, nitriles, and the azide ion are summarized.

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One-Step Synthesis of Heteroaromatic-Fused Pyrrolidines via Cyclopropane Ring-Opening Reaction: Application to the PKCβ Inhibitor JTT-010

Cited by 90 publications

References 26 publications

Synthesis and Some Biological Properties of Pyrrolo[1,2‐a]indoles

Synthesis and Some Biological Properties of Pyrrolo[1,2‐a]indoles

Reactions of Ruthenium–Allenylidene Complexes Tethering a Cyclopropyl Group

Ring Opening of Donor–Acceptor Cyclopropanes with N-Nucleophiles

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One-Step Synthesis of Heteroaromatic-Fused Pyrrolidines via Cyclopropane Ring-Opening Reaction: Application to the PKCβ Inhibitor JTT-010

Cited by 90 publications

References 26 publications

Synthesis and Some Biological Properties of Pyrrolo[1,2‐a]indoles

Synthesis and Some Biological Properties of Pyrrolo[1,2‐a]indoles

Reactions of Ruthenium–Allenylidene Complexes Tethering a Cyclopropyl Group

Ring Opening of Donor–Acceptor Cyclopropanes with N-Nucleo­philes

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Product

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Ring Opening of Donor–Acceptor Cyclopropanes with N-Nucleophiles