Synthesis of π-Extended Imidazoles by 1,3-Dipolar Cycloaddition of Polycyclic Aromatic Azomethine Ylides with Nitriles

Qiang Qiang Li; Kotaro Ochiai; Cherie Anne Lee; Shingo Ito

doi:10.1021/acs.orglett.0c02203

Synthesis of π-Extended Imidazoles by 1,3-Dipolar Cycloaddition of Polycyclic Aromatic Azomethine Ylides with Nitriles

Qiang Qiang Li, Kotaro Ochiai, Cherie Anne Lee, Shingo Ito^*

^*Corresponding author for this work

Nanyang Technological University

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

18 Citations (Scopus)

Abstract

Here we report the 1,3-dipolar cycloaddition of polycyclic aromatic azomethine ylides with nitriles to produce highly fused imidazole derivatives, that is, tribenzo[b,g,ij]imidazo[2,1,5-de]quinolizine. The advantages of this transformation are the broad substrate scope and the good functional group compatibility. The subsequent palladium-catalyzed intramolecular cyclization provides an efficient approach to further π-extended imidazoles, that is, 14b1,15-diazadibenzo[fg,ij]cyclopenta[rst]pentaphene.

Original language	English
Pages (from-to)	6132-6137
Number of pages	6
Journal	Organic Letters
Volume	22
Issue number	15
DOIs	https://doi.org/10.1021/acs.orglett.0c02203
Publication status	Published - Aug 7 2020
Externally published	Yes

Bibliographical note

Publisher Copyright:
Copyright © 2020 American Chemical Society.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Synthesis of π-Extended Imidazoles by 1,3-Dipolar Cycloaddition of Polycyclic Aromatic Azomethine Ylides with Nitriles",

abstract = "Here we report the 1,3-dipolar cycloaddition of polycyclic aromatic azomethine ylides with nitriles to produce highly fused imidazole derivatives, that is, tribenzo[b,g,ij]imidazo[2,1,5-de]quinolizine. The advantages of this transformation are the broad substrate scope and the good functional group compatibility. The subsequent palladium-catalyzed intramolecular cyclization provides an efficient approach to further π-extended imidazoles, that is, 14b1,15-diazadibenzo[fg,ij]cyclopenta[rst]pentaphene.",

author = "Li, {Qiang Qiang} and Kotaro Ochiai and Lee, {Cherie Anne} and Shingo Ito",

note = "Publisher Copyright: Copyright {\textcopyright} 2020 American Chemical Society.",

year = "2020",

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doi = "10.1021/acs.orglett.0c02203",

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T1 - Synthesis of π-Extended Imidazoles by 1,3-Dipolar Cycloaddition of Polycyclic Aromatic Azomethine Ylides with Nitriles

AU - Li, Qiang Qiang

AU - Ochiai, Kotaro

AU - Lee, Cherie Anne

AU - Ito, Shingo

PY - 2020/8/7

Y1 - 2020/8/7

N2 - Here we report the 1,3-dipolar cycloaddition of polycyclic aromatic azomethine ylides with nitriles to produce highly fused imidazole derivatives, that is, tribenzo[b,g,ij]imidazo[2,1,5-de]quinolizine. The advantages of this transformation are the broad substrate scope and the good functional group compatibility. The subsequent palladium-catalyzed intramolecular cyclization provides an efficient approach to further π-extended imidazoles, that is, 14b1,15-diazadibenzo[fg,ij]cyclopenta[rst]pentaphene.

AB - Here we report the 1,3-dipolar cycloaddition of polycyclic aromatic azomethine ylides with nitriles to produce highly fused imidazole derivatives, that is, tribenzo[b,g,ij]imidazo[2,1,5-de]quinolizine. The advantages of this transformation are the broad substrate scope and the good functional group compatibility. The subsequent palladium-catalyzed intramolecular cyclization provides an efficient approach to further π-extended imidazoles, that is, 14b1,15-diazadibenzo[fg,ij]cyclopenta[rst]pentaphene.

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Synthesis of π-Extended Imidazoles by 1,3-Dipolar Cycloaddition of Polycyclic Aromatic Azomethine Ylides with Nitriles

Abstract

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