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Volumn 13, Issue 5, 2011, Pages 1098-1101

Palladium-catalyzed highly regio-and stereoselective synthesis of 4-alkylidene-4 H -3,1-benzoxazines from N -Acyl-o -alkynylanilines

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; ANILINE DERIVATIVE; BENZOXAZINE DERIVATIVE; PALLADIUM;

EID: 79952140680     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol103130s     Document Type: Article
Times cited : (55)

References (57)
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    • Patil, N.T.1    Yamamoto, Y.2
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    • 2-aryl and 2-heteroaryl indole synthesis)
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    • Note
    • 2] (24 bar) and from that the 3,1-benzoxazines were formed as a mixture of E-and Z -isomers contaminated with a minor amount of the TMS-eliminated starting materials.
  • 55
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    • references cited therein. For our previous examples, see:;;; J. Chem. Soc., Chem. Commun. 1992, 22 (thermal electrocyclization)
    • Wang, H.; Liu, L.; Wang, Y.; Peng, C.; Zhang, J.; Zhu, Q. Tetrahedron Lett. 2009, 50, 6841 and references cited therein. For our previous examples, see: Saito, T.; Ohmori, H.; Furuno, E.; Motoki, S. J. Chem. Soc., Chem. Commun. 1992, 22 (thermal electrocyclization)
    • (2009) Tetrahedron Lett. , vol.50 , pp. 6841
    • Wang, H.1    Liu, L.2    Wang, Y.3    Peng, C.4    Zhang, J.5    Zhu, Q.6    Saito, T.7    Ohmori, H.8    Furuno, E.9    Motoki, S.10
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    • 13C NMR, IR, HRMS) and confirmed by X-ray crystallography of 2d and 2r: The crystallographic coordinates for 2r have been deposited with the Cambridge Crystallographic Data Centre; deposition no. 769241. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Rd., Cambridge CB2 1EZ, UK or via www.ccdc.cam.ac.uk/conts/retrieving.html. (see the Supporting Information). Noe was also observed between the olefinic-H and the peri-position-H of the benzene ring of 2, suggesting the Z -configuration.
    • 13C NMR, IR, HRMS) and confirmed by X-ray crystallography of 2d and 2r: The crystallographic coordinates for 2r have been deposited with the Cambridge Crystallographic Data Centre; deposition no. 769241. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Rd., Cambridge CB2 1EZ, UK or via www.ccdc.cam.ac.uk/conts/retrieving.html. (see the Supporting Information). Noe was also observed between the olefinic-H and the peri-position-H of the benzene ring of 2, suggesting the Z -configuration.


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