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Please use this identifier to cite or link to this item: http://hdl.handle.net/10198/815

Title: Novel synthetic routes to thienocarbazoles via palladium or copper catalyzed amination or amidation of arylhalides and intramolecular cyclization
Authors: Ferreira, Isabel C.F.R.
Queiroz, Maria João R.P.
Kirsch, Gilbert
Keywords: C–N coupling
Copper
Palladium
Cyclization–deprotection
Issue Date: 2002
Publisher: Elsevier
Citation: Ferreira, Isabel C.F.R.; Queiroz, Maria João R.P.; Kirsch, Gilbert (2002) - Novel synthetic routes to thienocarbazoles via palladium or copper catalyzed amination or amidation of arylhalides and intramolecular cyclization. Tetrahedron. ISSN 0040-4020. 58:39, p. 7943-7949
Abstract: Palladium or copper catalyzed aminations or amidations were performed to obtain diarylamines and diarylacetamides precursors of thienocarbazoles. The fact that an ortho-bromodiarylamine did not cyclize to the corresponding thienocarbazole under conditions known for carbazoles from ortho-halodiphenylamines, conducted us to a highly efficient method of palladium-catalyzed intramolecular cyclization with N-deprotection of ortho-halodiarylacetamides to thienocarbazoles. Other method of intramolecular cyclization of diarylamines based on the reoxidation of the Pd(0) formed by Cu(OAc)2, avoiding the use of stoichiometric amounts of Pd(OAc)2, gave thienocarbazoles in a moderate yield, including a ring A methoxylated compound. An attempt to combine palladium and copper catalyses in a ‘one pot’ reaction of amination and intramolecular cyclization gave as major product a N-benzo[b]thiophene substituted carbazole and the required thienocarbazole in low yield.
URI: http://hdl.handle.net/10198/815
ISSN: 0040-4020
Appears in Collections:BB - Artigos em Revistas Indexados ao ISI

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