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

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

20 引文斯高帕斯（Scopus）

摘要

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.

原文	英語
頁（從 - 到）	3242-3254
頁數	13
期刊	Advanced Synthesis and Catalysis
卷	357
發行號	14-15
DOIs	https://doi.org/10.1002/adsc.201500449
出版狀態	已發佈 - 2015 10月 1

ASJC Scopus subject areas

催化
有機化學

存取文件

10.1002/adsc.201500449

其它文件與鏈接

CCDC 1032867: Experimental Crystal Structure Determination
Yeh, M.-C. P. (Contributor), Liang, C.-J. (Contributor), Chen, H.-F. (Contributor) & Weng, Y.-T. (Contributor), Unknown Publisher, 2014
DOI: 10.5517/cc13ns9v, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc13ns9v&sid=DataCite
資料集: Dataset
CCDC 1032864: Experimental Crystal Structure Determination
Yeh, M.-C. P. (Contributor), Liang, C.-J. (Contributor), Chen, H.-F. (Contributor) & Weng, Y.-T. (Contributor), Unknown Publisher, 2014
DOI: 10.5517/cc13ns6r, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc13ns6r&sid=DataCite
資料集: Dataset
CCDC 1007050: Experimental Crystal Structure Determination
Yeh, M.-C. P. (Creator), Liang, C.-J. (Creator), Chen, H.-F. (Creator) & Weng, Y.-T. (Creator), Unknown Publisher, 2015
DOI: 10.5517/cc12sxh8, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc12sxh8&sid=DataCite
資料集: Dataset

引用此

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 等.
於: Advanced Synthesis and Catalysis, 卷 357, 編號 14-15, 01.10.2015, p. 3242-3254.

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

@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 - https://www.scopus.com/pages/publications/84944937317

UR - https://www.scopus.com/pages/publications/84944937317#tab=citedBy

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

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 1032867: Experimental Crystal Structure Determination

CCDC 1032864: Experimental Crystal Structure Determination

CCDC 1007050: Experimental Crystal Structure Determination

引用此