2005•Organic LettersRequires access

An Efficient and Simple Aminobenzannulation Reaction: Pyrrolidine as a Trigger for the Synthesis of 1-Amino-acridines

Philippe Belmont, Tahar Belhadj

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Abstract

[reaction: see text] A new aminobenzannulation methodology has been developed and applied successfully to the synthesis of 1-amino-acridines. The key and last step goes through an enamine intermediate that was detected in some cases. When pyrrolidine and powdered 4 A molecular sieves were used, the enamine synthesis and the aminobenzannulation step took place subsequently, whereas for other secondary amines, neutral Al(2)O(3) or PtCl(2) catalysis was necessary.

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[reaction: see text] A new aminobenzannulation methodology has been developed and applied successfully to the synthesis of 1-amino-acridines. The key and last step goes through an enamine intermediate that was detected in some cases. When pyrrolidine and powdered 4 A molecular sieves were used, the enamine synthesis and the aminobenzannulation step took place subsequently, whereas for other secondary amines, neutral Al(2)O(3) or PtCl(2) catalysis was necessary.

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Available abstract

[reaction: see text] A new aminobenzannulation methodology has been developed and applied successfully to the synthesis of 1-amino-acridines. The key and last step goes through an enamine intermediate that was detected in some cases. When pyrrolidine and powdered 4 A molecular sieves were used, the enamine synthesis and the aminobenzannulation step took place subsequently, whereas for other secondary amines, neutral Al(2)O(3) or PtCl(2) catalysis was necessary.

Key concepts: Enamine, Pyrrolidine, Chemistry, Catalysis, Combinatorial chemistry, Acridine derivatives, Molecular sieve, Organic chemistry

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