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

✍ Scribed by Chan Sik Cho; Tae Kyung Kim; Tae-Jeong Kim; Sang Chul Shim; Nam Sik Yoon

Book ID
102338901
Publisher
Journal of Heterocyclic Chemistry
Year
2002
Tongue
English
Weight
33 KB
Volume
39
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

Nitroarenes are reductively cyclized with 3‐amino‐1‐propanols in dioxane/H~2~O 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.

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