Synlett, Table of Contents Synlett 2018; 29(03): 310-313DOI: 10.1055/s-0036-1591506 letter © Georg Thieme Verlag Stuttgart · New YorkIodonium-Induced Cyclization of N-Allenylindoles and N-Allenylpyrroles: An Access to Iododihydropyrido[1,2-a]indoles and Dihydroindolizines Charlotte Grandclaudon a PSL Research University, Chimie ParisTech - CNRS, Institut de Recherche de Chimie Paris, 11 Rue P. et M. Curie, 75005 Paris, France , Veronique Michelet a PSL Research University, Chimie ParisTech - CNRS, Institut de Recherche de Chimie Paris, 11 Rue P. et M. Curie, 75005 Paris, France , Patrick Y. Toullec * a PSL Research University, Chimie ParisTech - CNRS, Institut de Recherche de Chimie Paris, 11 Rue P. et M. Curie, 75005 Paris, France b Institute of Molecular Sciences, University of Bordeaux, 351, Cours de la Libération, 33405 Talence, France Email: patrick.toullec@u-bordeaux.fr› Author AffiliationsRecommend Article Abstract Buy Article All articles of this category 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. Keywords Keywordselectrophilic iodocyclization - allenes - NIS - indoles - pyrroles Full Text References References and Notes 1a Aygun A. Pindur U. Curr. Med. Chem. 2003; 10: 1113 1b Leena Gupta BS. P. Archna Talwar BS. P. Prem MS. Chauhan BS. P. Curr. Med. 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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]+. Supplementary Material Supplementary Material Supporting Information
