Facile access to condensed arenothiophenes - Preparation of dihydrophenanthrothiophenes and dihydrophenanthro[1]benzothiophenes

Masataka Watanabe; Taisuke Matsumoto; Shuntaro Mataka; Thies Thiemann

doi:10.3184/030823405774308925

Facile access to condensed arenothiophenes - Preparation of dihydrophenanthrothiophenes and dihydrophenanthro[1]benzothiophenes

Masataka Watanabe, Taisuke Matsumoto, Shuntaro Mataka, Thies Thiemann

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

1 Citation (Scopus)

Abstract

4-Bromo-3-formyl-1,2-dihydronaphthalenes undergo Suzuki cross coupling and Wittig olefination reaction in a one pot procedure. The trienes obtained can be cyclised thermally under concomitant dehydrogenation to dihydrophenanthrothiophenes and dihydrophenanthro[1]benzothiophenes. An X-ray crystal structural analysis was carried out for ethyl (E)-3-[1-(1-benzothiophen- 3-yl)-3,4-dihydro-2-naphthyl]propenoate.

Original language	English
Pages (from-to)	564-571
Number of pages	8
Journal	Journal of Chemical Research
Issue number	9
DOIs	https://doi.org/10.3184/030823405774308925
Publication status	Published - Sept 2005
Externally published	Yes

Keywords

Electrocyclisation
One pot reaction
Suzuki coupling
Trienes
Wittig-olefination
X-ray crystal structure

ASJC Scopus subject areas

Chemistry(all)

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10.3184/030823405774308925

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title = "Facile access to condensed arenothiophenes - Preparation of dihydrophenanthrothiophenes and dihydrophenanthro[1]benzothiophenes",

abstract = "4-Bromo-3-formyl-1,2-dihydronaphthalenes undergo Suzuki cross coupling and Wittig olefination reaction in a one pot procedure. The trienes obtained can be cyclised thermally under concomitant dehydrogenation to dihydrophenanthrothiophenes and dihydrophenanthro[1]benzothiophenes. An X-ray crystal structural analysis was carried out for ethyl (E)-3-[1-(1-benzothiophen- 3-yl)-3,4-dihydro-2-naphthyl]propenoate.",

keywords = "Electrocyclisation, One pot reaction, Suzuki coupling, Trienes, Wittig-olefination, X-ray crystal structure",

author = "Masataka Watanabe and Taisuke Matsumoto and Shuntaro Mataka and Thies Thiemann",

year = "2005",

month = sep,

doi = "10.3184/030823405774308925",

language = "English",

pages = "564--571",

journal = "Journal of Chemical Research",

issn = "0308-2342",

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T1 - Facile access to condensed arenothiophenes - Preparation of dihydrophenanthrothiophenes and dihydrophenanthro[1]benzothiophenes

AU - Watanabe, Masataka

AU - Matsumoto, Taisuke

AU - Mataka, Shuntaro

AU - Thiemann, Thies

PY - 2005/9

Y1 - 2005/9

N2 - 4-Bromo-3-formyl-1,2-dihydronaphthalenes undergo Suzuki cross coupling and Wittig olefination reaction in a one pot procedure. The trienes obtained can be cyclised thermally under concomitant dehydrogenation to dihydrophenanthrothiophenes and dihydrophenanthro[1]benzothiophenes. An X-ray crystal structural analysis was carried out for ethyl (E)-3-[1-(1-benzothiophen- 3-yl)-3,4-dihydro-2-naphthyl]propenoate.

AB - 4-Bromo-3-formyl-1,2-dihydronaphthalenes undergo Suzuki cross coupling and Wittig olefination reaction in a one pot procedure. The trienes obtained can be cyclised thermally under concomitant dehydrogenation to dihydrophenanthrothiophenes and dihydrophenanthro[1]benzothiophenes. An X-ray crystal structural analysis was carried out for ethyl (E)-3-[1-(1-benzothiophen- 3-yl)-3,4-dihydro-2-naphthyl]propenoate.

KW - Electrocyclisation

KW - One pot reaction

KW - Suzuki coupling

KW - Trienes

KW - Wittig-olefination

KW - X-ray crystal structure

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DO - 10.3184/030823405774308925

M3 - Article

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SN - 0308-2342

SP - 564

EP - 571

JO - Journal of Chemical Research

JF - Journal of Chemical Research

IS - 9

ER -

Facile access to condensed arenothiophenes - Preparation of dihydrophenanthrothiophenes and dihydrophenanthro[1]benzothiophenes

Abstract

Keywords

ASJC Scopus subject areas

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