Indium(III)-Catalyzed Cyclization of Aromatic 5-Enynamides: Facile Synthesis of 2-Aminonaphthalenes, 2-Amino-1H-indenes, and 2,3-Dihydro-1H-indeno[2,1-b]pyridines

Ming Chang P. Yeh; Chia Jung Liang; Hsiao Feng Chen; Yu Ting Weng

doi:10.1002/adsc.201500449

Indium(III)-Catalyzed Cyclization of Aromatic 5-Enynamides: Facile Synthesis of 2-Aminonaphthalenes, 2-Amino-1H-indenes, and 2,3-Dihydro-1H-indeno[2,1-b]pyridines

Ming Chang P. Yeh^*, Chia Jung Liang, Hsiao Feng Chen, Yu Ting Weng

^*Corresponding author for this work

Department of Chemistry

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

19 Citations (Scopus)

Abstract

Indium(III)-catalyzed cyclization reactions of aromatic 5-enynamides were studied. Indium triflate enabled the efficient synthesis of 2-aminonaphthalenes and 2-amino-1H-indenes from aromatic N-methyl-N-tosyl-ynamides bearing an ortho-vinyl and -isobutenyl group, respectively. The aromatic N-3-arylpropargylynamides bearing an ortho-gem-dihalovinyl subunit underwent a tandem cyclization/carbobromination reaction in the presence of indium tribromide to provide the dibrominated 2,3-dihydro-1H-indeno[2,1-b]pyridine derivatives in good yields.

Original language	English
Pages (from-to)	3242-3254
Number of pages	13
Journal	Advanced Synthesis and Catalysis
Volume	357
Issue number	14-15
DOIs	https://doi.org/10.1002/adsc.201500449
Publication status	Published - 2015 Oct 1

Keywords

amides
bromine
cyclization
indium

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1002/adsc.201500449

Cite this

Indium(III)-Catalyzed Cyclization of Aromatic 5-Enynamides: Facile Synthesis of 2-Aminonaphthalenes, 2-Amino-1H-indenes, and 2,3-Dihydro-1H-indeno[2,1-b]pyridines. / Yeh, Ming Chang P.; Liang, Chia Jung; Chen, Hsiao Feng et al.
In: Advanced Synthesis and Catalysis, Vol. 357, No. 14-15, 01.10.2015, p. 3242-3254.

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

@article{350b48d27fdb462da4ac9af690b1bfbb,

title = "Indium(III)-Catalyzed Cyclization of Aromatic 5-Enynamides: Facile Synthesis of 2-Aminonaphthalenes, 2-Amino-1H-indenes, and 2,3-Dihydro-1H-indeno[2,1-b]pyridines",

abstract = "Indium(III)-catalyzed cyclization reactions of aromatic 5-enynamides were studied. Indium triflate enabled the efficient synthesis of 2-aminonaphthalenes and 2-amino-1H-indenes from aromatic N-methyl-N-tosyl-ynamides bearing an ortho-vinyl and -isobutenyl group, respectively. The aromatic N-3-arylpropargylynamides bearing an ortho-gem-dihalovinyl subunit underwent a tandem cyclization/carbobromination reaction in the presence of indium tribromide to provide the dibrominated 2,3-dihydro-1H-indeno[2,1-b]pyridine derivatives in good yields.",

keywords = "amides, bromine, cyclization, indium",

author = "Yeh, {Ming Chang P.} and Liang, {Chia Jung} and Chen, {Hsiao Feng} and Weng, {Yu Ting}",

note = "Publisher Copyright: {\textcopyright} 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

year = "2015",

month = oct,

day = "1",

doi = "10.1002/adsc.201500449",

language = "English",

volume = "357",

pages = "3242--3254",

journal = "Advanced Synthesis and Catalysis",

issn = "1615-4150",

publisher = "Wiley-VCH Verlag",

number = "14-15",

}

TY - JOUR

T1 - Indium(III)-Catalyzed Cyclization of Aromatic 5-Enynamides

T2 - Facile Synthesis of 2-Aminonaphthalenes, 2-Amino-1H-indenes, and 2,3-Dihydro-1H-indeno[2,1-b]pyridines

AU - Yeh, Ming Chang P.

AU - Liang, Chia Jung

AU - Chen, Hsiao Feng

AU - Weng, Yu Ting

PY - 2015/10/1

Y1 - 2015/10/1

N2 - Indium(III)-catalyzed cyclization reactions of aromatic 5-enynamides were studied. Indium triflate enabled the efficient synthesis of 2-aminonaphthalenes and 2-amino-1H-indenes from aromatic N-methyl-N-tosyl-ynamides bearing an ortho-vinyl and -isobutenyl group, respectively. The aromatic N-3-arylpropargylynamides bearing an ortho-gem-dihalovinyl subunit underwent a tandem cyclization/carbobromination reaction in the presence of indium tribromide to provide the dibrominated 2,3-dihydro-1H-indeno[2,1-b]pyridine derivatives in good yields.

AB - Indium(III)-catalyzed cyclization reactions of aromatic 5-enynamides were studied. Indium triflate enabled the efficient synthesis of 2-aminonaphthalenes and 2-amino-1H-indenes from aromatic N-methyl-N-tosyl-ynamides bearing an ortho-vinyl and -isobutenyl group, respectively. The aromatic N-3-arylpropargylynamides bearing an ortho-gem-dihalovinyl subunit underwent a tandem cyclization/carbobromination reaction in the presence of indium tribromide to provide the dibrominated 2,3-dihydro-1H-indeno[2,1-b]pyridine derivatives in good yields.

KW - amides

KW - bromine

KW - cyclization

KW - indium

UR - http://www.scopus.com/inward/record.url?scp=84944937317&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84944937317&partnerID=8YFLogxK

U2 - 10.1002/adsc.201500449

DO - 10.1002/adsc.201500449

M3 - Article

AN - SCOPUS:84944937317

SN - 1615-4150

VL - 357

SP - 3242

EP - 3254

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 14-15

ER -

Indium(III)-Catalyzed Cyclization of Aromatic 5-Enynamides: Facile Synthesis of 2-Aminonaphthalenes, 2-Amino-1H-indenes, and 2,3-Dihydro-1H-indeno[2,1-b]pyridines

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

CCDC 1032867: Experimental Crystal Structure Determination

CCDC 1052571: Experimental Crystal Structure Determination

CCDC 1007050: Experimental Crystal Structure Determination

Cite this

Indium(III)-Catalyzed Cyclization of Aromatic 5-Enynamides: Facile Synthesis of 2-Aminonaphthalenes, 2-Amino-1H-indenes, and 2,3-Dihydro-1H-indeno[2,1-b]pyridines

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 1032867: Experimental Crystal Structure Determination

CCDC 1052571: Experimental Crystal Structure Determination

CCDC 1007050: Experimental Crystal Structure Determination

Cite this