Concise synthesis of 2-N-hydroxy-3, 4-dihydroisoquinol-2-one: A bacterial siderophore and human 5-lipooxygenase inhibitor. Issue 15 (11th April 2018)

• Record Type: Journal Article
• Authors: Tutov, Anna; Bakulina, Olga; Dar'in, Dmitry; Krasavin, Mikhail
• Is Part Of: Tetrahedron letters. Volume 59:Issue 15(2018)
• Page Start: 1511
• Page End: 1512
• Publication Date: 2018-04-11
• Subjects: Castagnoli-Cushman reaction -- Formaldoxime -- Decarboxylation -- O-Debenzylation; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.03.017
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Shorter, more high-yielding synthesis of an important N -hydroxylactam is described. The synthesis is based on the Castagnoli-Cushman reaction. Persistent impurity described in the literature was formed. The impurity was separated after total decarboxylation of the product mixture. Carboxylic acid version of 2- N -hydroxy-3, 4-dihydroisoquinol-2-one was obtained. Abstract: A short synthesis of 2- N -hydroxy-3, 4-dihydroisoquinol-2-one has been devised, which is based on the Castagnoli-Cushman reaction and 3 times more high-yielding compared to an earlier reported sequence.