Synthesis of Halogenated Cyclic Enamines from Cyclic N-2-En-4-ynyl-N-1-ynylamides and N-Propargyl-N-1-ynylamides via a Tandem Iron Halide Promoted N-to-C Shift-Aza-Prins Cyclization Sequence

Hsin Hui Lin, Tai Ching Chiang, Rong Xuan Wu, Yi Mei Chang, Hao Wen Wang, Ssu Ting Liu, Ming-Chang P. Yeh

Research output: Contribution to journalArticle

Abstract

A facile and efficient N-to-C allyl shift-aza-Prins cyclization sequence of cyclic N-2-en-4-ynyl-N-1-ynylamides is promoted by iron(III) chloride, generating chloro-containing bridged bicyclic enamines in minutes and in high yields. This reaction involves an unprecedented formation of a ketenimine via Fe(III)-mediated N-to-C allyl rearrangement, followed by aza-Prins cyclization. This sequence can also be applied to the generation of brominated cyclobutenamine derivatives using Fe(III) bromide and N-propargyl-N-1-ynylamides. (Figure presented.).

Original languageEnglish
JournalAdvanced Synthesis and Catalysis
DOIs
Publication statusPublished - 2019 Jan 1

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Cyclization
Iron
Bromides
Chlorides
Derivatives
N-propargyl
ketenimine

Keywords

  • Cyclization
  • Halogenation
  • Rearrangement

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Synthesis of Halogenated Cyclic Enamines from Cyclic N-2-En-4-ynyl-N-1-ynylamides and N-Propargyl-N-1-ynylamides via a Tandem Iron Halide Promoted N-to-C Shift-Aza-Prins Cyclization Sequence. / Lin, Hsin Hui; Chiang, Tai Ching; Wu, Rong Xuan; Chang, Yi Mei; Wang, Hao Wen; Liu, Ssu Ting; Yeh, Ming-Chang P.

In: Advanced Synthesis and Catalysis, 01.01.2019.

Research output: Contribution to journalArticle

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abstract = "A facile and efficient N-to-C allyl shift-aza-Prins cyclization sequence of cyclic N-2-en-4-ynyl-N-1-ynylamides is promoted by iron(III) chloride, generating chloro-containing bridged bicyclic enamines in minutes and in high yields. This reaction involves an unprecedented formation of a ketenimine via Fe(III)-mediated N-to-C allyl rearrangement, followed by aza-Prins cyclization. This sequence can also be applied to the generation of brominated cyclobutenamine derivatives using Fe(III) bromide and N-propargyl-N-1-ynylamides. (Figure presented.).",
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T1 - Synthesis of Halogenated Cyclic Enamines from Cyclic N-2-En-4-ynyl-N-1-ynylamides and N-Propargyl-N-1-ynylamides via a Tandem Iron Halide Promoted N-to-C Shift-Aza-Prins Cyclization Sequence

AU - Lin, Hsin Hui

AU - Chiang, Tai Ching

AU - Wu, Rong Xuan

AU - Chang, Yi Mei

AU - Wang, Hao Wen

AU - Liu, Ssu Ting

AU - Yeh, Ming-Chang P.

PY - 2019/1/1

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N2 - A facile and efficient N-to-C allyl shift-aza-Prins cyclization sequence of cyclic N-2-en-4-ynyl-N-1-ynylamides is promoted by iron(III) chloride, generating chloro-containing bridged bicyclic enamines in minutes and in high yields. This reaction involves an unprecedented formation of a ketenimine via Fe(III)-mediated N-to-C allyl rearrangement, followed by aza-Prins cyclization. This sequence can also be applied to the generation of brominated cyclobutenamine derivatives using Fe(III) bromide and N-propargyl-N-1-ynylamides. (Figure presented.).

AB - A facile and efficient N-to-C allyl shift-aza-Prins cyclization sequence of cyclic N-2-en-4-ynyl-N-1-ynylamides is promoted by iron(III) chloride, generating chloro-containing bridged bicyclic enamines in minutes and in high yields. This reaction involves an unprecedented formation of a ketenimine via Fe(III)-mediated N-to-C allyl rearrangement, followed by aza-Prins cyclization. This sequence can also be applied to the generation of brominated cyclobutenamine derivatives using Fe(III) bromide and N-propargyl-N-1-ynylamides. (Figure presented.).

KW - Cyclization

KW - Halogenation

KW - Rearrangement

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