Synthesis of poly condensed oxygen-containing helical heterocycles via rearrangement of benzofused-2,2′-diphenoquinone derivatives

Md Sharif Hossain; Shota Inoue; Mohammad Shahabuddin; Takao Kimura; Michinori Karikomi

doi:10.1016/j.tetlet.2019.05.050

Synthesis of poly condensed oxygen-containing helical heterocycles via rearrangement of benzofused-2,2′-diphenoquinone derivatives

Md Sharif Hossain, Shota Inoue, Mohammad Shahabuddin, Takao Kimura, Michinori Karikomi

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

2 Citations (Scopus)

Abstract

The thermal rearrangement reaction of helical-shaped quinone (benzofused-2,2′-diphenoquinone derivative) afforded three types of poly-condensed oxygen-containing heterocyclic compounds. One type of them was spiro compound which is consisting of cyclopentadiene and γ-butyrolactone. The other two compounds were helically condensed compounds, one of them containing as cyclopentadiene and pyranone ring and the other consists of fused furan and oxepin ring. These products were could be selectively synthesized by the choosing modification of reaction conditions. Moreover, the mechanistic aspects of these reactions are also discussed.

Original language	English
Pages (from-to)	1682-1685
Number of pages	4
Journal	Tetrahedron Letters
Volume	60
Issue number	25
DOIs	https://doi.org/10.1016/j.tetlet.2019.05.050
Publication status	Published - Jun 20 2019
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2019.05.050

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title = "Synthesis of poly condensed oxygen-containing helical heterocycles via rearrangement of benzofused-2,2′-diphenoquinone derivatives",

abstract = "The thermal rearrangement reaction of helical-shaped quinone (benzofused-2,2′-diphenoquinone derivative) afforded three types of poly-condensed oxygen-containing heterocyclic compounds. One type of them was spiro compound which is consisting of cyclopentadiene and γ-butyrolactone. The other two compounds were helically condensed compounds, one of them containing as cyclopentadiene and pyranone ring and the other consists of fused furan and oxepin ring. These products were could be selectively synthesized by the choosing modification of reaction conditions. Moreover, the mechanistic aspects of these reactions are also discussed.",

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T1 - Synthesis of poly condensed oxygen-containing helical heterocycles via rearrangement of benzofused-2,2′-diphenoquinone derivatives

AU - Hossain, Md Sharif

AU - Inoue, Shota

AU - Shahabuddin, Mohammad

AU - Kimura, Takao

AU - Karikomi, Michinori

PY - 2019/6/20

Y1 - 2019/6/20

N2 - The thermal rearrangement reaction of helical-shaped quinone (benzofused-2,2′-diphenoquinone derivative) afforded three types of poly-condensed oxygen-containing heterocyclic compounds. One type of them was spiro compound which is consisting of cyclopentadiene and γ-butyrolactone. The other two compounds were helically condensed compounds, one of them containing as cyclopentadiene and pyranone ring and the other consists of fused furan and oxepin ring. These products were could be selectively synthesized by the choosing modification of reaction conditions. Moreover, the mechanistic aspects of these reactions are also discussed.

AB - The thermal rearrangement reaction of helical-shaped quinone (benzofused-2,2′-diphenoquinone derivative) afforded three types of poly-condensed oxygen-containing heterocyclic compounds. One type of them was spiro compound which is consisting of cyclopentadiene and γ-butyrolactone. The other two compounds were helically condensed compounds, one of them containing as cyclopentadiene and pyranone ring and the other consists of fused furan and oxepin ring. These products were could be selectively synthesized by the choosing modification of reaction conditions. Moreover, the mechanistic aspects of these reactions are also discussed.

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Synthesis of poly condensed oxygen-containing helical heterocycles via rearrangement of benzofused-2,2′-diphenoquinone derivatives

Abstract

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