2,2,3-Tribromopropanal as a Versatile Reagent in the Skraup-Type Synthesis of 3-Bromoquinolin-6-ols

Abstract 2,2,3-Tribromopropanal, a reagent which almost became forgotten in the chemical literature after its first application in the 1950s, is used for the one-step transformation of diversely substituted 4-nitro- and 4-methoxyanilines into 3-bromo-6-nitroquinolines and 3-bromo-6-methoxyquinolines...

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Bibliographic Details
Published in:Synlett 2014-04, Vol.25 (6), p.858-862
Main Authors: Lamberth, Clemens, Kessabi, Fiona Murphy, Beaudegnies, Renaud, Quaranta, Laura, Trah, Stephan, Berthon, Guillaume, Cederbaum, Fredrik, Vettiger, Thomas, Prasanna, CS
Format: Article
Language:English
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Summary:Abstract 2,2,3-Tribromopropanal, a reagent which almost became forgotten in the chemical literature after its first application in the 1950s, is used for the one-step transformation of diversely substituted 4-nitro- and 4-methoxyanilines into 3-bromo-6-nitroquinolines and 3-bromo-6-methoxyquinolines. These intermediates are then converted, in one further step, into 3-bromoquinolin-6-ols, which may carry additional substituents at positions 7 and 8.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0033-1340670