Organic Letters
Letter
1830709).15 When 10 mmol of 3a reacted with H2SO4 for 10 h,
benzoxazinone 5a was obtained in 72% yield.
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In summary, we have demonstrated a novel nitrosation and
iron(III)-catalyzed C−C bond cleavage of easily available 2-
arylindoles for the synthesis of various valuable 2-amino-
benzonitriles in good to excellent yields. Benzoxazinones were
obtained easily in good yields by simple operations. This
method not only provides a new approach to 2-amino-
benzonitriles and benzoxazinones but also expands the
applications of C−C bond cleavage of indole materials.
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ASSOCIATED CONTENT
* Supporting Information
The Supporting Information is available free of charge on the
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S
Experimental procedures; characteristic data; spectra of
compounds 2, 3, 4, and 5 (PDF)
García Mancheno, O.; Bolm, C. Chem. Soc. Rev. 2008, 37, 1108.
̃
Accession Codes
(c) Junge, K.; Schroder, K.; Beller, M. Chem. Commun. 2011, 47, 4849.
̈
lographic data for this paper. These data can be obtained free of
Cambridge Crystallographic Data Centre, 12 Union Road,
Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
(d) Bauer, I.; Knolker, H.-J. Chem. Rev. 2015, 115, 3170.
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(d) Zhao, M.-N.; Ren, Z.-H.; Yu, L.; Wang, Y.-Y.; Guan, Z.-H. Org.
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AUTHOR INFORMATION
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Corresponding Author
ORCID
(11) (a) Shang, X.-X.; Vu, H.-M.; Li, X.-Q. Synthesis 2018, 50, 377.
(b) Yamashita, M.; Nishizono, Y.; Himekawa, S.; Iida, A. Tetrahedron
2016, 72, 4123.
(12) (a) Ma, X.-P.; Li, K.; Wu, S.-Y.; Liang, C.; Su, G.-F.; Mo, D.-L.
Green Chem. 2017, 19, 5761. (b) Ma, X.-P.; Zhu, J.-F.; Wu, S.-Y.;
Chen, C.-H.; Zou, N.; Liang, C.; Su, G.-F.; Mo, D.-L. J. Org. Chem.
2017, 82, 502. (c) Shi, W.-M.; Li, X.-H.; Liang, C.; Mo, D.-L. Adv.
Synth. Catal. 2017, 359, 4129. (d) Wang, Z.-X.; Shi, W.-M.; Bi, H.-Y.;
Li, X.-H.; Su, G.-F.; Mo, D.-L. J. Org. Chem. 2016, 81, 8014.
(13) For selected examples for nitrosation by the TBN reagent, see:
(a) Li, P.; Jia, X. Synthesis 2018, 50, 711. (b) Yu, J.; Lu, M. Org. Biomol.
Chem. 2015, 13, 7397. (c) Yang, X.-H.; Ouyang, X.-H.; Wei, W.-T.;
Author Contributions
†W.-L.C. and S.-Y.W. contributed equally.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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Song, R.-J.; Li, J.-H. Adv. Synth. Catal. 2015, 357, 1161. (d) Buchi, G.;
̈
Financial support from the National Natural Science
Foundation of China (21562005, 21602037), the Natural
Science Foundation of Guangxi (2015GXNSFCA139001,
2016GXNSFFA380005), the Ministry of Education of China
(IRT_16R15), and the “Overseas 100 Talents Program” of
Guangxi Higher Education are greatly appreciated.
Lee, G. C. M.; Yang, D.; Tannenbaum, S. R. J. Am. Chem. Soc. 1986,
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(15) The X-ray structure of 5a was previously reported; see:
Thilagavathy, R.; Kavitha, H. P.; Arulmozhi, R.; Vennila, J. P.;
Manivannan, V. Acta Crystallogr., Sect. E: Struct. Rep. Online 2009, 65,
o127.
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