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

Chang You Sie, Che-Ping Chuang

Research output: Contribution to journalArticle

1 Citation (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 languageEnglish
Pages (from-to)5483-5491
Number of pages9
JournalOrganic and Biomolecular Chemistry
Volume16
Issue number30
DOIs
Publication statusPublished - 2018 Jan 1

Fingerprint

Azepines
Benzazepines
Cyclization
Dione
Iodine
Functional groups
iodine
Derivatives
synthesis
1,4-naphthoquinone

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Sie, Chang You ; Chuang, Che-Ping. / Electrophilic carbocyclization reactions of 2-(2-alkynylphenyl)amino-1,4-naphthoquinones. In: Organic and Biomolecular Chemistry. 2018 ; Vol. 16, No. 30. pp. 5483-5491.
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Electrophilic carbocyclization reactions of 2-(2-alkynylphenyl)amino-1,4-naphthoquinones. / Sie, Chang You; Chuang, Che-Ping.

In: Organic and Biomolecular Chemistry, Vol. 16, No. 30, 01.01.2018, p. 5483-5491.

Research output: Contribution to journalArticle

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