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^*

^*Corresponding author for this work

Department of Chemistry and Materials Science

Chiba University

Research output: Contribution to journal › Article › Scientific › peer-review

2 Citations (Scopus)

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.

Original language	English
Article number	151754
Number of pages	4
Journal	Tetrahedron Letters
Volume	61
Issue number	15
DOIs	https://doi.org/10.1016/j.tetlet.2020.151754
Publication status	Published - 9 Apr 2020
MoE publication type	A1 Journal article-refereed

Keywords

Cascade reactions
Radical reactions
Benzofurans
Synthetic methods
DIPTOINDONESIN G
CARBOCYCLES
INSERTION
MALIBATOL

Access to Document

10.1016/j.tetlet.2020.151754

Cite this

@article{1534096c83604e0186a5d67fda83edab,

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",

month = apr,

day = "9",

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

language = "English",

volume = "61",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "15",

}

TY - JOUR

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 - http://www.scopus.com/inward/record.url?scp=85080069990&partnerID=8YFLogxK

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

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this