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Synlett 2018; 29(03): 310-313
DOI: 10.1055/s-0036-1591506
DOI: 10.1055/s-0036-1591506
letter
Iodonium-Induced Cyclization of N-Allenylindoles and N-Allenylpyrroles: An Access to Iododihydropyrido[1,2-a]indoles and Dihydroindolizines
This work was supported by the Ministère de l’Education et de la Recherche, the Centre National de la Recherche Scientifique (CNRS), and the Agence Nationale de la Recherche. C.G. is grateful to the Agence Nationale de la Recherche (ANR-13-JS07-0010) for a doctoral grant (2013–2016).Further Information
Publication History
Received: 25 July 2017
Accepted after revision: 02 October 2017
Publication Date:
14 November 2017 (online)
![](https://www.thieme-connect.de/media/synlett/201803/lookinside/thumbnails/st-2017-d0577-l_10-1055_s-0036-1591506-1.jpg)
Abstract
The formation of iodinated dihydropyrido[1,2-a]indoles and dihydroindolizines was achieved by an iodocarbocyclization reaction of N-allenylindoles and N-allenylpyrroles. This transformation proceeded under very mild conditions using N-iodosuccinimide as the electrophilic iodine source to deliver the products via a 6-endo cyclization process. Careful choice of the solvent and concentration were mandatory to obtain the cyclization in good yields.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591506.
- Supporting Information
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- 17 General Procedure for the Iodocyclization of Allenyl Substrates To a dry flask equipped with a magnetic stir bar were added the allenyl substrate (0.2 mmol, 1 equiv) and CH3CN (5 mL); then NIS (0.24 mmol, 1.2 equiv) dissolved in CH3CN (5 mL) was added. After stirring at room temperature for 10 min, TLC analysis showed complete conversion of the substrate, and the reaction mixture was quenched with sat. aq Na2S2O3 (5 mL). The aqueous phase was extracted with EtOAc (2 × 10 mL), the combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure to afford the crude product, which was then purified by flash chromatography to give the desired cyclized compound. Compound 2b was obtained as a colorless oil in 75% yield (53.4 mg). Rf = 0.38 (petroleum ether/dichloromethane = 95:5). 1H NMR (300 MHz, CDCl3): δ = 7.57 (dd, J = 6.7, 1.5 Hz, 1 H), 7.26–7.09 (m, 3 H), 4.57 (s, 2 H), 2.44 (s, 3 H), 2.14 (s, 3 H), 1.62 (s, 6 H). 13C NMR (75 MHz, CDCl3): δ = 134.7 (Cq), 133.6 (Cq), 130.2 (Cq), 129.5 (Cq), 120.9 (CH), 119.5 (CH), 117.9 (CH), 115.9 (Cq), 108.6 (CH), 104.5 (Cq), 46.8 (CH2), 40.7 (Cq), 30.5 (2CH3), 28.5 (CH3), 10.9 (CH3). APCI-MS: m/z = 352 [M + H]+.
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