Radical cascade cyclization for synthesizing 3,4-fused tricyclic benzofuran derivatives

Masaya Nakajima; Yusuke Kondo; Shun-ichi Nakano; Yusuke Adachi; Dongil Choi; Robert Franzen; Tetsuhiro Nemoto

doi:10.1016/j.tetlet.2020.151754

Radical cascade cyclization for synthesizing 3,4-fused tricyclic benzofuran derivatives

Masaya Nakajima
, Yusuke Kondo
, Shun-ichi Nakano
, Yusuke Adachi
, Dongil Choi
, Robert Franzen
, Tetsuhiro Nemoto^*

^*Tämän työn vastaava kirjoittaja

Kemian ja materiaalitieteen laitos

Chiba University

Tutkimustuotos: Lehtiartikkeli › Article › Scientific › vertaisarvioitu

2 Sitaatiot (Scopus)

Abstrakti

A new method for synthesizing 3,4-fused tricyclic 3-alkylidene dihydrobenzofuran derivatives was developed. Treatment of propargyl iodophenol derivatives with a tethered alkene at the three contiguous positions under the radical cascade reaction conditions induced the reaction of the generated vinyl radical intermediates with the internal alkene, producing tricyclic 3-alkylidene dihydrobenzofurans in 25%-93% yield. The reaction products could be utilized as the precursors for 3,4-fused tricyclic benzofurans. (C) 2020 Elsevier Ltd. All rights reserved.

Alkuperäiskieli	Englanti
Artikkeli	151754
Sivumäärä	4
Julkaisu	Tetrahedron Letters
Vuosikerta	61
Numero	15
DOI - pysyväislinkit	https://doi.org/10.1016/j.tetlet.2020.151754
Tila	Julkaistu - 9 huhtik. 2020
OKM-julkaisutyyppi	A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä

Rahoitus

This work was supported by JSPS KAKENHI Grant Number 18H025550, and The Naito Foundation.

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10.1016/j.tetlet.2020.151754

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title = "Radical cascade cyclization for synthesizing 3,4-fused tricyclic benzofuran derivatives",

abstract = "A new method for synthesizing 3,4-fused tricyclic 3-alkylidene dihydrobenzofuran derivatives was developed. Treatment of propargyl iodophenol derivatives with a tethered alkene at the three contiguous positions under the radical cascade reaction conditions induced the reaction of the generated vinyl radical intermediates with the internal alkene, producing tricyclic 3-alkylidene dihydrobenzofurans in 25\%-93\% yield. The reaction products could be utilized as the precursors for 3,4-fused tricyclic benzofurans. (C) 2020 Elsevier Ltd. All rights reserved.",

keywords = "Cascade reactions, Radical reactions, Benzofurans, Synthetic methods, DIPTOINDONESIN G, CARBOCYCLES, INSERTION, MALIBATOL",

author = "Masaya Nakajima and Yusuke Kondo and Shun-ichi Nakano and Yusuke Adachi and Dongil Choi and Robert Franzen and Tetsuhiro Nemoto",

year = "2020",

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doi = "10.1016/j.tetlet.2020.151754",

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T1 - Radical cascade cyclization for synthesizing 3,4-fused tricyclic benzofuran derivatives

AU - Nakajima, Masaya

AU - Kondo, Yusuke

AU - Nakano, Shun-ichi

AU - Adachi, Yusuke

AU - Choi, Dongil

AU - Franzen, Robert

AU - Nemoto, Tetsuhiro

PY - 2020/4/9

Y1 - 2020/4/9

N2 - A new method for synthesizing 3,4-fused tricyclic 3-alkylidene dihydrobenzofuran derivatives was developed. Treatment of propargyl iodophenol derivatives with a tethered alkene at the three contiguous positions under the radical cascade reaction conditions induced the reaction of the generated vinyl radical intermediates with the internal alkene, producing tricyclic 3-alkylidene dihydrobenzofurans in 25%-93% yield. The reaction products could be utilized as the precursors for 3,4-fused tricyclic benzofurans. (C) 2020 Elsevier Ltd. All rights reserved.

AB - A new method for synthesizing 3,4-fused tricyclic 3-alkylidene dihydrobenzofuran derivatives was developed. Treatment of propargyl iodophenol derivatives with a tethered alkene at the three contiguous positions under the radical cascade reaction conditions induced the reaction of the generated vinyl radical intermediates with the internal alkene, producing tricyclic 3-alkylidene dihydrobenzofurans in 25%-93% yield. The reaction products could be utilized as the precursors for 3,4-fused tricyclic benzofurans. (C) 2020 Elsevier Ltd. All rights reserved.

KW - Cascade reactions

KW - Radical reactions

KW - Benzofurans

KW - Synthetic methods

KW - DIPTOINDONESIN G

KW - CARBOCYCLES

KW - INSERTION

KW - MALIBATOL

UR - https://www.scopus.com/pages/publications/85080069990

U2 - 10.1016/j.tetlet.2020.151754

DO - 10.1016/j.tetlet.2020.151754

M3 - Article

SN - 0040-4039

VL - 61

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 15

M1 - 151754

ER -

Radical cascade cyclization for synthesizing 3,4-fused tricyclic benzofuran derivatives

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