☆ 4.4 Article

High-yielding synthesis of 1-isoindolinone derivatives via palladium-catalysed cycloaminocarbonylation

TETRAHEDRON (2011)

期刊

TETRAHEDRON

卷 67, 期 5, 页码 1036-1040

出版社

PERGAMON-ELSEVIER SCIENCE LTD

DOI: 10.1016/j.tet.2010.11.099

关键词

Aminocarbonylation; Cyclocarbonylation; Carbon monoxide; Palladium; Lactam; Amino acid

类别

Chemistry, Organic

资金

Hungarian Research Fund [CK78553, NK77784]

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Protocol

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摘要

1-Isoindolinone derivatives were synthesised in high yields (up to 89%) by using 2-iodobenzyl bromide and 2-iodobenzylamine as bifunctional substrates in palladium-catalysed carbonylation. Depending on the N-nucleophiles, two types of compounds were synthesised with 2-iodobenzyl bromide: the use of primary amines, including amino acid methylesters, resulted in the formation of N-substituted 1-isoindolinones, while secondary amines react both with the benzyl bromide and iodoarene moieties resulting in the corresponding ortho-(N-piperidino/morpholinomethyl)-benzamides. The parent 1-isoindolinone was obtained in a facile, highly chemoselective intramolecular aminocarbonylation of 2-iodobenzylamine. The mechanistic details of the ring-closure reaction and the conditions leading to side-products are discussed as well. (C) 2010 Elsevier Ltd. All rights reserved.

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