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Yuan YC, Yang HB, Tang XY, et al. Unprecedented Oxycyanation of Methylenecyclopropanes for the Facile Synthesis of Benzoxazine Compounds Containing a Cyano Group. Chemistry. 2016;22(15):5146-50doi: 10.1002/chem.201505224.
Yuan, Y. C., Yang, H. B., Tang, X. Y., Wei, Y., & Shi, M. (2016). Unprecedented Oxycyanation of Methylenecyclopropanes for the Facile Synthesis of Benzoxazine Compounds Containing a Cyano Group. Chemistry (Weinheim an der Bergstrasse, Germany), 22(15), 5146-50. https://doi.org/10.1002/chem.201505224
Yuan, Yu-Chao, et al. "Unprecedented Oxycyanation of Methylenecyclopropanes for the Facile Synthesis of Benzoxazine Compounds Containing a Cyano Group." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,15 (2016): 5146-50. doi: https://doi.org/10.1002/chem.201505224
Yuan YC, Yang HB, Tang XY, Wei Y, Shi M. Unprecedented Oxycyanation of Methylenecyclopropanes for the Facile Synthesis of Benzoxazine Compounds Containing a Cyano Group. Chemistry. 2016 Apr 04;22(15):5146-50. doi: 10.1002/chem.201505224. Epub 2016 Feb 26. PMID: 26868457.
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Chemistry. 2016 Apr 04;22(15):5146-50. doi: 10.1002/chem.201505224. Epub 2016 Feb 26.

Unprecedented Oxycyanation of Methylenecyclopropanes for the Facile Synthesis of Benzoxazine Compounds Containing a Cyano Group.

Chemistry (Weinheim an der Bergstrasse, Germany)

Yu-Chao Yuan, Hai-Bin Yang, Xiang-Ying Tang, Yin Wei, Min Shi

Affiliations

  1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.
  2. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China. [email protected].
  3. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China. [email protected].
  4. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China. [email protected].

PMID: 26868457 DOI: 10.1002/chem.201505224

Abstract

A novel intramolecular oxycyanation of methylenecyclopropanes is reported that proceeds through oxidative cleavage of the N-CN bond and subsequent palladium transfer from N to O of the amide group. A range of substituted benzo[d][1,3]oxazines with a cyano group are readily furnished by this newly developed oxycyanation reaction. Tris(4-trifluoromethylphenyl)phosphine as a ligand has been found to be crucial to effectively promote the transformation with high chemo- and regioselectivity. Moreover, the reaction outcome can be significantly affected by the electronic effect of the acyl group attached to the nitrogen atom of methylenecyclopropanes. When R(3) is a chloromethyl group, the pyrrolo[2,3-b]quinoline derivative is obtained by thermal-induced [3+2] cycloaddition of methylenecyclopropane to the methanediimine intermediate.

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: amides; benzoxazines; intramolecular oxycyanation; palladium; synthetic methods

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