Silver-Mediated Intramolecular Friedel-Crafts-Type Cyclizations of 2-Benzyloxy-3-bromoindolines: Synthesis of Isochromeno[3,4-b[ indolines and 3-Arylindoles

Toshiki Yamashiro; Koji Yamada; Haruka Yoshida; Yutaro Tomisaka; Takahide Nishi; Takumi Abe

doi:10.1055/s-0039-1690734

Silver-Mediated Intramolecular Friedel-Crafts-Type Cyclizations of 2-Benzyloxy-3-bromoindolines: Synthesis of Isochromeno[3,4-b[ indolines and 3-Arylindoles

Toshiki Yamashiro, Koji Yamada, Haruka Yoshida, Yutaro Tomisaka, Takahide Nishi, Takumi Abe

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

8 Citations (Scopus)

Abstract

We disclose a silver-mediated intramolecular Friedel-Crafts-type cyclization of 2-benzyloxy-3-bromoindolines to afford an untapped family of isochromeno[3,4-b[indolines and 3-arylindoles, in which deformylative arylation of 2-(4-methoxybenzyloxy)-3-bromoindolines is reported for the first time. The isochromeno[3,4-b[indolines can be readily transformed into other heterocyclic moieties.

Original language	English
Pages (from-to)	2247-2252
Number of pages	6
Journal	Synlett
Volume	30
Issue number	20
DOIs	https://doi.org/10.1055/s-0039-1690734
Publication status	Published - 2019
Externally published	Yes

Keywords

3-arylindoles
Friedel-Crafts
cyclization
deformylative arylation
isochromeno[3,4-b[indolines
silver

ASJC Scopus subject areas

Organic Chemistry

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10.1055/s-0039-1690734

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title = "Silver-Mediated Intramolecular Friedel-Crafts-Type Cyclizations of 2-Benzyloxy-3-bromoindolines: Synthesis of Isochromeno[3,4-b[ indolines and 3-Arylindoles",

abstract = "We disclose a silver-mediated intramolecular Friedel-Crafts-type cyclization of 2-benzyloxy-3-bromoindolines to afford an untapped family of isochromeno[3,4-b[indolines and 3-arylindoles, in which deformylative arylation of 2-(4-methoxybenzyloxy)-3-bromoindolines is reported for the first time. The isochromeno[3,4-b[indolines can be readily transformed into other heterocyclic moieties.",

keywords = "3-arylindoles, Friedel-Crafts, cyclization, deformylative arylation, isochromeno[3,4-b[indolines, silver",

author = "Toshiki Yamashiro and Koji Yamada and Haruka Yoshida and Yutaro Tomisaka and Takahide Nishi and Takumi Abe",

note = "Funding Information: This work was financially supported by a Grant-in-Aid for Young Scientists (B) (Grant No. 16K18849 for T. A.) from the Japan Society for the Promotion of Science (JSPS).JapanSocietyforthePromotionofScience(16K18849) Publisher Copyright: {\textcopyright} 2019 Georg Thieme Verlag. All rights reserved.",

year = "2019",

doi = "10.1055/s-0039-1690734",

language = "English",

volume = "30",

pages = "2247--2252",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "20",

}

TY - JOUR

T1 - Silver-Mediated Intramolecular Friedel-Crafts-Type Cyclizations of 2-Benzyloxy-3-bromoindolines

T2 - Synthesis of Isochromeno[3,4-b[ indolines and 3-Arylindoles

AU - Yamashiro, Toshiki

AU - Yamada, Koji

AU - Yoshida, Haruka

AU - Tomisaka, Yutaro

AU - Nishi, Takahide

AU - Abe, Takumi

N1 - Funding Information: This work was financially supported by a Grant-in-Aid for Young Scientists (B) (Grant No. 16K18849 for T. A.) from the Japan Society for the Promotion of Science (JSPS).JapanSocietyforthePromotionofScience(16K18849) Publisher Copyright: © 2019 Georg Thieme Verlag. All rights reserved.

PY - 2019

Y1 - 2019

N2 - We disclose a silver-mediated intramolecular Friedel-Crafts-type cyclization of 2-benzyloxy-3-bromoindolines to afford an untapped family of isochromeno[3,4-b[indolines and 3-arylindoles, in which deformylative arylation of 2-(4-methoxybenzyloxy)-3-bromoindolines is reported for the first time. The isochromeno[3,4-b[indolines can be readily transformed into other heterocyclic moieties.

AB - We disclose a silver-mediated intramolecular Friedel-Crafts-type cyclization of 2-benzyloxy-3-bromoindolines to afford an untapped family of isochromeno[3,4-b[indolines and 3-arylindoles, in which deformylative arylation of 2-(4-methoxybenzyloxy)-3-bromoindolines is reported for the first time. The isochromeno[3,4-b[indolines can be readily transformed into other heterocyclic moieties.

KW - 3-arylindoles

KW - Friedel-Crafts

KW - cyclization

KW - deformylative arylation

KW - isochromeno[3,4-b[indolines

KW - silver

UR - http://www.scopus.com/inward/record.url?scp=85075973257&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85075973257&partnerID=8YFLogxK

U2 - 10.1055/s-0039-1690734

DO - 10.1055/s-0039-1690734

M3 - Article

AN - SCOPUS:85075973257

SN - 0936-5214

VL - 30

SP - 2247

EP - 2252

JO - Synlett

JF - Synlett

IS - 20

ER -

Silver-Mediated Intramolecular Friedel-Crafts-Type Cyclizations of 2-Benzyloxy-3-bromoindolines: Synthesis of Isochromeno[3,4-b[ indolines and 3-Arylindoles

Abstract

Keywords

ASJC Scopus subject areas

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