Ruthenium-catalyzed synthesis of quinolines via reductive heteroannulation of nitroarenes with 3-amino-1-propanols

Chan Sik Cho; Tae Kyung Kim; Tae Jeong Kim; Sang Chul Shim; Nam Sik Yoon

doi:10.1002/jhet.5570390207

Ruthenium-catalyzed synthesis of quinolines via reductive heteroannulation of nitroarenes with 3-amino-1-propanols

Chan Sik Cho, Tae Kyung Kim, Tae Jeong Kim, Sang Chul Shim, Nam Sik Yoon

Department of Applied Chemistry

Kyungpook National University

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

10 Scopus citations

Abstract

Nitroarenes are reductively cyclized with 3-amino-1-propanols in dioxane/H₂O in the presence of a ruthenium catalyst and tin(II) chloride dihydrate together with isopropanol to afford the corresponding quinolines. A reaction pathway involving initial reduction of nitroarenes to anilines, propanol group transfer from 3-amino-1-propanols to anilines, N-alkylation of anilines by 3-anilino-1-propanols and heteroannulation of 1, 3-dianilinopropanes is proposed.

Original language	English
Pages (from-to)	291-294
Number of pages	4
Journal	Journal of Heterocyclic Chemistry
Volume	39
Issue number	2
DOIs	https://doi.org/10.1002/jhet.5570390207
State	Published - 1 Jan 2002

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title = "Ruthenium-catalyzed synthesis of quinolines via reductive heteroannulation of nitroarenes with 3-amino-1-propanols",

abstract = "Nitroarenes are reductively cyclized with 3-amino-1-propanols in dioxane/H2O in the presence of a ruthenium catalyst and tin(II) chloride dihydrate together with isopropanol to afford the corresponding quinolines. A reaction pathway involving initial reduction of nitroarenes to anilines, propanol group transfer from 3-amino-1-propanols to anilines, N-alkylation of anilines by 3-anilino-1-propanols and heteroannulation of 1, 3-dianilinopropanes is proposed.",

author = "Cho, {Chan Sik} and Kim, {Tae Kyung} and Kim, {Tae Jeong} and Shim, {Sang Chul} and Yoon, {Nam Sik}",

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T1 - Ruthenium-catalyzed synthesis of quinolines via reductive heteroannulation of nitroarenes with 3-amino-1-propanols

AU - Cho, Chan Sik

AU - Kim, Tae Kyung

AU - Kim, Tae Jeong

AU - Shim, Sang Chul

AU - Yoon, Nam Sik

PY - 2002/1/1

Y1 - 2002/1/1

N2 - Nitroarenes are reductively cyclized with 3-amino-1-propanols in dioxane/H2O in the presence of a ruthenium catalyst and tin(II) chloride dihydrate together with isopropanol to afford the corresponding quinolines. A reaction pathway involving initial reduction of nitroarenes to anilines, propanol group transfer from 3-amino-1-propanols to anilines, N-alkylation of anilines by 3-anilino-1-propanols and heteroannulation of 1, 3-dianilinopropanes is proposed.

AB - Nitroarenes are reductively cyclized with 3-amino-1-propanols in dioxane/H2O in the presence of a ruthenium catalyst and tin(II) chloride dihydrate together with isopropanol to afford the corresponding quinolines. A reaction pathway involving initial reduction of nitroarenes to anilines, propanol group transfer from 3-amino-1-propanols to anilines, N-alkylation of anilines by 3-anilino-1-propanols and heteroannulation of 1, 3-dianilinopropanes is proposed.

UR - http://www.scopus.com/inward/record.url?scp=0036096109&partnerID=8YFLogxK

U2 - 10.1002/jhet.5570390207

DO - 10.1002/jhet.5570390207

M3 - Article

AN - SCOPUS:0036096109

SN - 0022-152X

VL - 39

SP - 291

EP - 294

JO - Journal of Heterocyclic Chemistry

JF - Journal of Heterocyclic Chemistry

IS - 2

ER -

Ruthenium-catalyzed synthesis of quinolines via reductive heteroannulation of nitroarenes with 3-amino-1-propanols

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