期刊
TETRAHEDRON
卷 67, 期 47, 页码 9122-9128出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.09.095
关键词
Aminocarbonylation; Hydrazinocarbonylation; Carbon monoxide; Palladium; Tetrahydrophthalazine; Amino acid
资金
- Hungarian Research Fund [CK78553]
- Developing Competitiveness of Universities in the South Transdanubian Region [SROP-4.2.1.B-10/2/KONV-2010-0002]
1,2,3,4-Tetrahydrophthalazin-1-one and 1,2,3,4-tetrahydrophthalazin-1,4-dione derivatives were synthesised in high (up to 85%) and low yields using 2-iodobenzyl bromide and 1,2-diiodobenzene as bifunctional substrates, respectively. Iodoarenes, carbon monoxide and various hydrazine derivatives as N-nucleophiles were used in a three-component palladium-catalysed cascade hydrazinocarbonylation. A similar palladium-catalysed reaction, the aminocarbonylation of 1,2-diiodobenzene, resulted mainly in the formation of two types of major products depending on the amine N-nucleophiles: the use of primary amines yielded N-substituted phthalimides in double carbonylation, while secondary amines react with one of the iodoarene functionalities affording the corresponding 2-iodobenzamides. Due to double carbon monoxide insertion at one or both iodoarene functionalities, ketocarboxamide-carboxamide or bis-ketocarboxamide derivatives could be isolated by the modification of the reaction conditions. Some mechanistic details of the ring-closure reactions and the conditions leading to side-products are also discussed. (C) 2011 Elsevier Ltd. All rights reserved.
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