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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 50, 2020 - Issue 9
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SYNTHETIC COMMUNICATIONS REVIEWS

Access to polycyclic carbazoles from ring-fused 2-(9H-carbazol-1-yl)anilines

Wayland E. NolandDepartment of Chemistry, University of Minnesota, Minneapolis, MN, USAORCID Iconhttp://orcid.org/0000-0001-8183-0767View further author information
ORCID Icon,
Christopher D. BrownDepartment of Chemistry, University of Minnesota, Minneapolis, MN, USAView further author information
,
Kenneth J. TritchDepartment of Chemistry, University of Minnesota, Minneapolis, MN, USAView further author information
&
Andrew K. SchneererDepartment of Chemistry, University of Minnesota, Minneapolis, MN, USACorrespondence[email protected]
ORCID Iconhttp://orcid.org/0000-0003-0861-822XView further author information
ORCID Icon
Pages 1388-1395 | Received 05 Feb 2020, Published online: 19 Mar 2020

References

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  • Schmidt, A.; Reddy, K.; Knölker, H. Occurrence, Biogenesis, and Synthesis of Biologically Active Carbazole Alkaloids. Chem. Rev. 2012, 112, 3193–3328. DOI: 10.1021/cr200447s.
  • Aggarwal, T.; Sushmita, S.; Verma, A. K. Recent Advances in the Synthesis of Carbazoles from Indoles. Org. Biomol. Chem. 2019, 17, 8330–8342. DOI: 10.1039/C9OB01381D.
  • Wahlström, N.; Slätt, J.; Stensland, B.; Ertan, A.; Bergman, J.; Janosik, T. Synthetic Applications of Cyanoacetylated Bisindoles: Synthesis of Novel Cycloheptadiindoles, Indolocarbazoles, and Related Aza Analogues. J. Org. Chem. 2007, 72, 5886–5889. DOI: 10.1021/jo0706729.
  • Noland, W. E.; Brown, C. D.; Zabronsky, A. E.; Tritch, K. J. Synthesis of 2-(9H-Carbazol-1-yl)Anilines from 2,3′-Biindolyl and Ketones. Tetrahedron 2018, 74, 2391–2404. DOI: 10.1016/j.tet.2018.03.066.
  • Wang, H.; Wang, Z.; Huang, H.; Tan, J.; Xu, K. KOtBu-Promoted Oxidation of (Hetero)Benzylic Csp3–H to Ketones with Molecular Oxygen. Org. Lett. 2016, 18, 5680–5683. DOI: 10.1021/acs.orglett.6b02914.
  • (a) Simpson, J. C. E. Cinnolines. part VII. Further Observations of the Widman-Stoermer Reaction. J. Chem. Soc. 1946, 673–675. DOI: 10.1016/S0968-0896(02)00604-1. (b) Yu, Y.; Singh, S. K.; Liu, A.; Li, T.-K.; Liu, L. F.; LaVoie, E. J. Substituted Dibenzo[c,h]Cinnolines: Topoisomerase I-Targeting Anticancer Agents. Bioorg. Med. Chem 2003, 11, 1475–1491. DOI: 10.1039/JR9460000673.
  • Crystallographic data for 13 are deposited at the Cambridge Crystallographic Data Centre, deposition number 1948201. http://www.ccdc.cam.ac.uk/structures/.

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