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Volumn 63, Issue 3, 2007, Pages 690-702

Sequential palladium-catalysed C- and N-arylation reactions as a practical and general protocol for the synthesis of the first series of oxcarbazepine analogues

Author keywords

Analogues; Cross coupling; Oxcarbazepine; Palladium

Indexed keywords

10,11 DIHYDRO 5 AMINOCARBONYL 5H 1,3 DIFLUORO 7,8 DOMETHOXYDIBENZO[B,F] AZEPIN 10 ONE; 10,11 DIHYDRO 5 AMINOCARBONYL 5H 1,3 DIFLUORODIBENZO[B,F]AZEPIN 10 ONE; 10,11 DIHYDRO 5 AMINOCARBONYL 5H 2,3 DIMETHYLDIBENZO[B,F]AZEPIN 10 ONE; 10,11 DIHYDRO 5 AMINOCARBONYL 5H 2,3,7,8 TETRAMETHOXYDIBENZO[B,F]AZEPIN 10 ONE; 9,10 DIHYDRO 4 AMINOCARBONYL 4H 6,7 DIMETHYLTHIENO[3,2,B][F]BENZAZEPIN 10 ONE; 9,10 DIHYDRO 4 AMINOCARBONYL 4H THIENO[3,2,B][F]BENZAZEPIN 10 ONE; CARBON; NITROGEN; OXCARBAZEPINE; PALLADIUM;

EID: 33845441141     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.11.003     Document Type: Article
Times cited : (37)

References (44)
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    • After the optimisation of the synthetic route to OXC, we found in the literature an interesting study on the effect of the addition of small amounts of water in the palladium-catalysed amidation reactions. As in our case, the role of water was especially determining when the base was cesium carbonate and the solvents were either toluene or 1,4-dioxane. See:
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    • The only related example reported in the literature was developed by Hartwig's research group and involves the palladium-catalysed α-arylation of 2-acetylthiophene with bromobenzene, rendering the corresponding product in 68% yield. See:
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    • note
    • For a selection of the reaction conditions employed in the optimisation of this step, see the Supplementary data of this paper.
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    • The tendency of the sulfur atom to strongly coordinate with palladium is well-established. It is anticipated that poisoning the catalyst in this manner will inhibit the reaction progress and therefore account for the long reaction times required for these transformations. See:
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.