Synthesis of Carbazole Analogs via Grob Fragmentation of Norbornyl α-Diketones

Kadavergu, S and Agrawal, S K and Chintada, N R and Khan, Faiz Ahmed (2016) Synthesis of Carbazole Analogs via Grob Fragmentation of Norbornyl α-Diketones. Tetrahedron Letters, 57 (31). pp. 3449-3452. ISSN 0040-4039

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Abstract

A regioselective synthesis of carbazole analogs belonging to both the categories of natural origin, viz, microorganisms and higher plant source is reported. The synthesis of carbazole derivatives possessing a methylester group at C-1 position has been achieved by Cadogan cyclization of nitro bi-phenyl derivatives. Whereas, the carbazole analog possessing a methylester group at C-3 position was synthesized by Buchwald-Hartwig Pd-catalyzed cyclization of amino bi-phenyl derivatives. Suitably substituted bi-phenyl precursors were accessed from norbornyl α-diketones via Grob fragmentation, O-methylation and DBU aromatization reaction sequence. The reported carbazole derivatives posses structural features that are common with many carbazole natural products: Mukonine, Clausine-L, Murrayafoline-A and their sibling natural products.

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IITH Creators:
IITH CreatorsORCiD
Khan, Faiz AhmedUNSPECIFIED
Item Type: Article
Uncontrolled Keywords: Diketones; Fragmentation; Aromatization; Bi-phenyls; Cadogan cyclization; Pd-catalyzed cyclization; Carbazoles
Subjects: Chemistry
Divisions: Department of Chemistry
Depositing User: Team Library
Date Deposited: 28 Jun 2016 08:22
Last Modified: 21 Sep 2017 06:18
URI: http://raiithold.iith.ac.in/id/eprint/2490
Publisher URL: https://doi.org/10.1016/j.tetlet.2016.06.080
OA policy: http://www.sherpa.ac.uk/romeo/issn/0040-4039/
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