Aromatization Process for the Rapid Construction of [2,3-c]Dihydrocarbazoles and [2,3-c]Carbazoles.
Org Lett. 2017 09 01; 19(17):4476-4479.OL

Abstract

An intramolecular cascade amination/cyclization/aromatization reaction of functionalized alkylidenecyclopropanes has been developed in the presence of silver acetate, affording a variety of [2,3-c]dihydrocarbazoles and [2,3-c]carbazoles in moderate to excellent yields. The mechanistic investigations revealed that this cascade reaction proceeds through a radical initiated process. Moreover, further transformations for the synthesis of eustifoline-D and an OLED exhibit a potential synthetic utility of this method.

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Authors+Show Affiliations

Fan X

Yu LZ

Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology , 130 Mei Long Road, Shanghai 200237, People's Republic of China.

Wei Y

Shi M

State Key Laboratory of Organometallic Chemistry, University of Chinese Academy of Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 354 Fenglin Lu, Shanghai 200032, People's Republic of China. Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology , 130 Mei Long Road, Shanghai 200237, People's Republic of China.

Pub Type(s)

Journal Article

Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

28829142

Citation

Fan, Xing, et al. "Cascade Amination/Cyclization/Aromatization Process for the Rapid Construction of [2,3-c]Dihydrocarbazoles and [2,3-c]Carbazoles." Organic Letters, vol. 19, no. 17, 2017, pp. 4476-4479.

Fan X, Yu LZ, Wei Y, et al. Cascade Amination/Cyclization/Aromatization Process for the Rapid Construction of [2,3-c]Dihydrocarbazoles and [2,3-c]Carbazoles. Org Lett. 2017;19(17):4476-4479.

Fan, X., Yu, L. Z., Wei, Y., & Shi, M. (2017). Cascade Amination/Cyclization/Aromatization Process for the Rapid Construction of [2,3-c]Dihydrocarbazoles and [2,3-c]Carbazoles. Organic Letters, 19(17), 4476-4479. https://doi.org/10.1021/acs.orglett.7b01957

Fan X, et al. Cascade Amination/Cyclization/Aromatization Process for the Rapid Construction of [2,3-c]Dihydrocarbazoles and [2,3-c]Carbazoles. Org Lett. 2017 09 1;19(17):4476-4479. PubMed PMID: 28829142.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - Cascade Amination/Cyclization/Aromatization Process for the Rapid Construction of [2,3-c]Dihydrocarbazoles and [2,3-c]Carbazoles. AU - Fan,Xing, AU - Yu,Liu-Zhu, AU - Wei,Yin, AU - Shi,Min, Y1 - 2017/08/22/ PY - 2017/8/23/pubmed PY - 2017/8/23/medline PY - 2017/8/23/entrez SP - 4476 EP - 4479 JF - Organic letters JO - Org Lett VL - 19 IS - 17 N2 - An intramolecular cascade amination/cyclization/aromatization reaction of functionalized alkylidenecyclopropanes has been developed in the presence of silver acetate, affording a variety of [2,3-c]dihydrocarbazoles and [2,3-c]carbazoles in moderate to excellent yields. The mechanistic investigations revealed that this cascade reaction proceeds through a radical initiated process. Moreover, further transformations for the synthesis of eustifoline-D and an OLED exhibit a potential synthetic utility of this method. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/28829142/Cascade_Amination/Cyclization/Aromatization_Process_for_the_Rapid_Construction_of_[23_c]Dihydrocarbazoles_and_[23_c]Carbazoles_ L2 - https://doi.org/10.1021/acs.orglett.7b01957 DB - PRIME DP - Unbound Medicine ER -

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Cascade Amination/Cyclization/Aromatization Process for the Rapid Construction of [2,3-c]Dihydrocarbazoles and [2,3-c]Carbazoles.Org Lett. 2017 09 01; 19(17):4476-4479.OL