Electrophilic carbocyclization reactions of 2-(2-alkynylphenyl)amino-1,4-naphthoquinones

Chang You Sie; Che Ping Chuang

doi:10.1039/c8ob01170b

Electrophilic carbocyclization reactions of 2-(2-alkynylphenyl)amino-1,4-naphthoquinones

Chang You Sie, Che Ping Chuang

Department of Chemistry

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

6 Citations (Scopus)

Abstract

An efficient Ag(i)-catalyzed method for the synthesis of 5H-benzo[b]naphtho[2,3-f]azepine-6,11-diones from 2-(2-ethynylphenyl)amino substituted 1,4-naphthoquinones has been developed. In this transformation new C-C bond formation occurred regioselectively via a 7-endo-dig cyclization. The related 13-iodine substituted benzazepine derivatives could also be produced exclusively by the I₂-induced carbocyclization reaction of 2-(2-alkynylphenyl)amino substituted 1,4-naphthoquinones. This process has advantages such as mild reaction conditions and tolerance of a broad range of functional groups.

Original language	English
Pages (from-to)	5483-5491
Number of pages	9
Journal	Organic and Biomolecular Chemistry
Volume	16
Issue number	30
DOIs	https://doi.org/10.1039/c8ob01170b
Publication status	Published - 2018

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1039/c8ob01170b

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title = "Electrophilic carbocyclization reactions of 2-(2-alkynylphenyl)amino-1,4-naphthoquinones",

abstract = "An efficient Ag(i)-catalyzed method for the synthesis of 5H-benzo[b]naphtho[2,3-f]azepine-6,11-diones from 2-(2-ethynylphenyl)amino substituted 1,4-naphthoquinones has been developed. In this transformation new C-C bond formation occurred regioselectively via a 7-endo-dig cyclization. The related 13-iodine substituted benzazepine derivatives could also be produced exclusively by the I2-induced carbocyclization reaction of 2-(2-alkynylphenyl)amino substituted 1,4-naphthoquinones. This process has advantages such as mild reaction conditions and tolerance of a broad range of functional groups.",

author = "Sie, {Chang You} and Chuang, {Che Ping}",

note = "Funding Information: We are grateful to the Ministry of Science and Technology, ROC for financial support (Grant No. MOST-104-2113-M-006-003).",

year = "2018",

doi = "10.1039/c8ob01170b",

language = "English",

volume = "16",

pages = "5483--5491",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - Electrophilic carbocyclization reactions of 2-(2-alkynylphenyl)amino-1,4-naphthoquinones

AU - Sie, Chang You

AU - Chuang, Che Ping

N1 - Funding Information: We are grateful to the Ministry of Science and Technology, ROC for financial support (Grant No. MOST-104-2113-M-006-003).

PY - 2018

Y1 - 2018

N2 - An efficient Ag(i)-catalyzed method for the synthesis of 5H-benzo[b]naphtho[2,3-f]azepine-6,11-diones from 2-(2-ethynylphenyl)amino substituted 1,4-naphthoquinones has been developed. In this transformation new C-C bond formation occurred regioselectively via a 7-endo-dig cyclization. The related 13-iodine substituted benzazepine derivatives could also be produced exclusively by the I2-induced carbocyclization reaction of 2-(2-alkynylphenyl)amino substituted 1,4-naphthoquinones. This process has advantages such as mild reaction conditions and tolerance of a broad range of functional groups.

AB - An efficient Ag(i)-catalyzed method for the synthesis of 5H-benzo[b]naphtho[2,3-f]azepine-6,11-diones from 2-(2-ethynylphenyl)amino substituted 1,4-naphthoquinones has been developed. In this transformation new C-C bond formation occurred regioselectively via a 7-endo-dig cyclization. The related 13-iodine substituted benzazepine derivatives could also be produced exclusively by the I2-induced carbocyclization reaction of 2-(2-alkynylphenyl)amino substituted 1,4-naphthoquinones. This process has advantages such as mild reaction conditions and tolerance of a broad range of functional groups.

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SN - 1477-0520

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EP - 5491

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 30

ER -

Electrophilic carbocyclization reactions of 2-(2-alkynylphenyl)amino-1,4-naphthoquinones

Abstract

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