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Facile synthesis of 5H-benzo[b]carbazol-6-yl ketones via sequential reaction of Cu-catalyzed Friedel-Crafts alkylation, iodine-promoted cyclization, nucleophilic substitution and aromatization.
Org Biomol Chem. 2014 Sep 21; 12(35):6806-11.OB

Abstract

A convenient method to access 5H-benzo[b]carbazol-6-yl ketones via a sequential Cu-catalyzed Friedel-Crafts alkylation reaction of indoles with 2-(2-(alkynyl)benzylidene)malonates and iodine-promoted electrophilic cyclization followed by nucleophilic substitution and aromatization was developed. The products of the functional 5H-benzo[b]carbazol-6-yl ketones were obtained with up to 98% yield.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Wu J
Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China. bswan@dicp.ac.cn.
Wang D
No affiliation info available
Wang H
No affiliation info available
Wu F
No affiliation info available
Li X
No affiliation info available
Wan B
No affiliation info available

MeSH

AlkylationAlkynesCatalysisChemistry, OrganicCopperCyclizationIndolesIodineKetonesMalonatesMetalsMolecular StructureReproducibility of Results

Pub Type(s)

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

Language

eng

PubMed ID

25070224

Citation

Wu, Jing, et al. "Facile Synthesis of 5H-benzo[b]carbazol-6-yl Ketones Via Sequential Reaction of Cu-catalyzed Friedel-Crafts Alkylation, Iodine-promoted Cyclization, Nucleophilic Substitution and Aromatization." Organic & Biomolecular Chemistry, vol. 12, no. 35, 2014, pp. 6806-11.
Wu J, Wang D, Wang H, et al. Facile synthesis of 5H-benzo[b]carbazol-6-yl ketones via sequential reaction of Cu-catalyzed Friedel-Crafts alkylation, iodine-promoted cyclization, nucleophilic substitution and aromatization. Org Biomol Chem. 2014;12(35):6806-11.
Wu, J., Wang, D., Wang, H., Wu, F., Li, X., & Wan, B. (2014). Facile synthesis of 5H-benzo[b]carbazol-6-yl ketones via sequential reaction of Cu-catalyzed Friedel-Crafts alkylation, iodine-promoted cyclization, nucleophilic substitution and aromatization. Organic & Biomolecular Chemistry, 12(35), 6806-11. https://doi.org/10.1039/c4ob00815d
Wu J, et al. Facile Synthesis of 5H-benzo[b]carbazol-6-yl Ketones Via Sequential Reaction of Cu-catalyzed Friedel-Crafts Alkylation, Iodine-promoted Cyclization, Nucleophilic Substitution and Aromatization. Org Biomol Chem. 2014 Sep 21;12(35):6806-11. PubMed PMID: 25070224.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Facile synthesis of 5H-benzo[b]carbazol-6-yl ketones via sequential reaction of Cu-catalyzed Friedel-Crafts alkylation, iodine-promoted cyclization, nucleophilic substitution and aromatization. AU - Wu,Jing, AU - Wang,Dongping, AU - Wang,Haolong, AU - Wu,Fan, AU - Li,Xincheng, AU - Wan,Boshun, PY - 2014/7/30/entrez PY - 2014/7/30/pubmed PY - 2015/6/2/medline SP - 6806 EP - 11 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 12 IS - 35 N2 - A convenient method to access 5H-benzo[b]carbazol-6-yl ketones via a sequential Cu-catalyzed Friedel-Crafts alkylation reaction of indoles with 2-(2-(alkynyl)benzylidene)malonates and iodine-promoted electrophilic cyclization followed by nucleophilic substitution and aromatization was developed. The products of the functional 5H-benzo[b]carbazol-6-yl ketones were obtained with up to 98% yield. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/25070224/Facile_synthesis_of_5H_benzo[b]carbazol_6_yl_ketones_via_sequential_reaction_of_Cu_catalyzed_Friedel_Crafts_alkylation_iodine_promoted_cyclization_nucleophilic_substitution_and_aromatization_ DB - PRIME DP - Unbound Medicine ER -