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Ruthenium‐catalyzed synthesis of quinolines via reductive heteroannulation of nitroarenes with 3‐amino‐1‐propanols
Author(s) -
Cho Chan Sik,
Kim Tae Kyung,
Kim TaeJeong,
Shim Sang Chul,
Yoon Nam Sik
Publication year - 2002
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570390207
Subject(s) - chemistry , ruthenium , catalysis , alkylation , tin , chloride , transfer hydrogenation , chloroacetyl chloride , medicinal chemistry , combinatorial chemistry , organic chemistry
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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