Synthesis of bicyclopyrroles with various substituents at the bridging positions

Ito, Satoshi; Tobata, Marina; Asakura, Minenari; Shinozaki, Yasutaka; Iwabe, Yuuki; Sakamoto, Lisa; Ito, Shun-pei; Roppongi, Makoto; Oba, Toru

doi:10.1016/j.tetlet.2017.09.056

Tetrahedron Letters

2017

DOI: 10.1016/j.tetlet.2017.09.056

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Synthesis of bicyclopyrroles with various substituents at the bridging positions

Satoshi Ito

Marina Tobata

Minenari Asakura

et al.

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Cited by 3 publications

(2 citation statements)

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“…Diformyltripyrrane 5 was treated with 3a in the presence of TFA, followed by oxidation with p -chloranil to give a mixture of porphyrin-like products and the desired 6 in 2% yield together with 7 in 5% yield via an inverse-type 3 + 1 procedure . The fused bicyclo[3.2.1]octene ring of 7 should be formed via the skeletal 1,2-shift rearrangement of the BCOD moiety . The structures of 6 and 7 were confirmed by X-ray analysis, as shown in Figures S1 and S2.…”

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Synthesis of Peripherally Annulated Phenanthroporphyrins

et al. 2023

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Synthesis of unusual phenanthroporphyrins was achieved by a stepwise precursor method. Precursor porphyrins fused with aryl-substituted bicyclo[2.2.2]octadiene afforded the corresponding arylbenzoporphyrins (arylBPs) by a retro Diels− Alder reaction. Unusual phenanthroporphyrins were obtained via the intramolecular Scholl reaction of arylBPs. X-ray crystallographic analysis revealed a distorted, helical porphyrin plane. Redshifted absorptions of tetraphenanthroporphyrin are observed at ca. 580 nm for the B band and at 700−900 nm for the Q bands. Analysis of magnetic circular dichroism spectra and timedependent density functional theory calculations was used to explain the optical properties and electronic structures.

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Synthesis of Peripherally Annulated Phenanthroporphyrins

et al. 2023

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“…6 More recently, Ito and co-workers reported the Suzuki-Miyaura coupling of brominated BCOD-fused pyrrole to give phenyl, 2-naphthyl, and methylBCODpyrroles, which could afford substituted TBPs. 7 We synthesized thiophene-substituted BCODpyrrole 12 as shown in Scheme 2. Suzuki-Miyaura coupling of 3 8 and 4 afforded 5 in 78% yield.…”

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Synthesis of Di(3-thienyl)benzoporphyrin

Okujima¹,

Muramatsu²,

Mori³

et al. 2019

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We have successfully synthesized 2,3-di(3-thienyl)benzo[b]porphyrin based on retro Diels-Alder reaction of bicyclo[2.2.2]octadiene(BCOD)-fused porphyrin and investigated its photoisomerization reaction. 1,2-Diarylethene skeletons are attractive due to the reversible photochemical ring-closure/opening reactions. 1 1,2-Bis(2,5-dimethyl-3-thienyl)ethene derivatives 1 are well-known as a photochromic compound, which could be isomerized into cyclohexadienes 2 under irradiation by UV light with change of the color (Scheme 1). These photochromic diarylethenes have been investigated as photoswitchable luminescent materials 2 and conductive molecular wire. 3 In 2001, two papers on 1,2-di(3-thienyl)perfluorocyclopentene bearing porphyrin were reported as photoswitchable fluorophore and phosphorophore. 4 These photochromic molecules showed reversible photoisomerization between their closed and open forms by irradiation with UV and visible light. In these molecules, dithienylperfluorocyclopentene moiety undergoes photoisomerization reaction, while porphyrin moiety shows photoluminescent property. In closed form, dihydrobenzodithiophene unit is not conjugated to porphyrin ring directly. Herein we report synthesis of 2,3-di(3-thienyl)benzo[b]porphyrin based on retro Diels-Alder reaction of bicyclo[2.2.2]octadiene(BCOD)-fused porphyrin precursor and its photoisomerization reaction. Scheme 1. Photo-induced ring-closure/opening reaction of 1,2-bis(2,5-dimethyl-3-thienyl)ethene

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Synthesis of π-conjugated asymmetric aza-BODIPYs via nitrosobicyclopyrroles

Mori

Asakura

Kobayashi

et al. 2022

Tetrahedron Letters

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Synthesis of bicyclopyrroles with various substituents at the bridging positions

Cited by 3 publications

References 18 publications

Synthesis of Peripherally Annulated Phenanthroporphyrins

Synthesis of Peripherally Annulated Phenanthroporphyrins

Synthesis of Di(3-thienyl)benzoporphyrin

Synthesis of π-conjugated asymmetric aza-BODIPYs via nitrosobicyclopyrroles

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