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J Org Chem. 2005 Sep 2;70(18):7371-5.

Synthesis of 4,5-dianilinophthalimide and related analogues for potential treatment of Alzheimer's disease via palladium-catalyzed amination.

Author information

1
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.

Abstract

DAPH (4,5-dianilinophthalimide) has previously been shown to reverse the formation of neurotoxic fibrils associated with Alzheimer's disease. We have developed a synthetic route to DAPH and structurally related analogues that employs palladium-catalyzed amination as the key bond-forming step. The requisite substrates are easily obtained, and their coupling with substituted anilines proceeds in generally high yields. Thus, a variety of DAPH analogues can be quickly accessed in a modular fashion. In addition, the route described herein should also be amenable to the incorporation of other classes of nucleophiles into the molecular framework.

PMID:
16122261
DOI:
10.1021/jo051096o
[Indexed for MEDLINE]

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