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Microwave-assisted transition-metal-catalyzed synthesis of N-shifted and ring-expanded buflavine analogues
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
2007 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 13, no 22, 6452-6460 p.Article in journal (Other academic) Published
Abstract [en]

Two novel and efficient strategies for the synthesis of hitherto unknown N-shifted and ring-expanded buflavine analogues are presented. Construction of the medium-sized ring system of the title molecules, a difficult task due to the high activation energy needed for the ring-closure with the additional rigidity imposed by the biaryl skeleton, was achieved by using Suzuki-Miyaura biaryl coupling and a ring-closing metathesis reaction as the key steps. The combination of a second-generation Grubbs catalyst and microwave irradiation proved to be highly useful in generating the otherwise difficult to obtain medium-sized ring system of the buflavine analogues.

Place, publisher, year, edition, pages
2007. Vol. 13, no 22, 6452-6460 p.
Keyword [en]
buflavine, cross-coupling, medium-sized rings, metathesis, microwave irradiation
National Category
Pharmaceutical Sciences
URN: urn:nbn:se:uu:diva-17538DOI: 10.1002/chem.200700177PubMedID: 17508369OAI: oai:DiVA.org:uu-17538DiVA: diva2:45309
Available from: 2008-06-30 Created: 2008-06-30 Last updated: 2010-03-25Bibliographically approved

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