Nucleophilic Addition of Amines to Ruthenium Carbenes: ortho‐(Alkynyloxy)benzylamine Cyclizations towards 1,3‐Benzoxazines

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Angew. Chem. Int. Ed. 2015, 54, 2724 –2728.pdf (255.5 KB)
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URI: http://hdl.handle.net/10347/23346
ISSN: 1433-7851
E-ISSN: 1521-3773
DOI: 10.1002/anie.201410284

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2015

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Wiley
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Abstract

A new ruthenium-catalyzed cyclization of ortho-(alkynyloxy)benzylamines to dihydro-1,3-benzoxazines is reported. The cyclization is thought to take place via the vinyl ruthenium carbene intermediates that are easily formed from Cp*RuCl(cod) and N2CHSiMe3. The mild reaction conditions and the efficiency of the procedure allow the easy preparation of a broad range of new 2-vinyl-2-substituted 1,3-benzoxazine derivatives. Rearrangement of an internal Csp atom in the starting material into a tetrasubstituted Csp3 atom in the final 1,3-benzoxazine is highly remarkable.

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NOTICE: This is the peer reviewed version of the following article: González-Rodríguez, C., Suárez, J. R., Varela, J. A., Saá, C. (2015). Nucleophilic Addition of Amines to Ruthenium Carbenes: ortho‐(Alkynyloxy)benzylamine Cyclizations towards 1,3‐Benzoxazines. Angew. Chem. Int. Ed., 54, 9, 2724-2728. [doi: 10.1002/anie.201410284]. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for self-archiving

Keywords

Benzoxazines| Carbenes| Cyclization| Rearrangements| Ruthenium

Bibliographic citation

González-Rodríguez, C., Suárez, J. R., Varela, J. A., Saá, C. (2015). Nucleophilic Addition of Amines to Ruthenium Carbenes: ortho‐(Alkynyloxy)benzylamine Cyclizations towards 1,3‐Benzoxazines. Angew. Chem. Int. Ed., 54, 9, 2724-2728

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This work was supported by MICINN [projects CTQ2011-28258 and Consolider Ingenio 2010 (CSD2007-00006)], Xunta de Galicia and the European Regional Development Fund (projects CN2011/054, GRC2014/032 and EM 2012/051). C. G.-R. thanks the MICINN for a Juan de la Cierva Contract (JCI-2011-09946)

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© 2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for self-archiving

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