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Palladium‐Catalyzed Three‐Component Approach to Promazine with Formation of One Carbon–Sulfur and Two Carbon–Nitrogen Bonds
Author(s) -
Dahl Troels,
Tornøe Christian W.,
BangAndersen Benny,
Nielsen Poul,
Jørgensen Morten
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200705209
Subject(s) - thioether , chemistry , intramolecular force , intermolecular force , amination , catalysis , ferrocene , palladium , aryl , yield (engineering) , promazine , sulfur , phenothiazine , nitrogen , carbon fibers , organic chemistry , combinatorial chemistry , medicinal chemistry , molecule , electrochemistry , materials science , electrode , composite material , composite number , metallurgy , endocrinology , medicine , alkyl , chlorpromazine , pharmacology
Zip it up! The use of a Pd/dppf catalyst gives access to the tricyclic phenothiazine scaffold starting from 1‐bromo‐2‐iodobenzenes, aliphatic or aromatic amines, and 2‐bromothiophenols in a single reaction flask (see scheme; dppf=1,1′‐bis(diphenylphosphanyl)ferrocene; dba=dibenzylidineacetone). This transformation involves thioether formation and subsequent intermolecular and intramolecular aryl amination reactions. The reaction occurs in good overall yield and selectivity.