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Synlett 2021; 32(09): 930-934
DOI: 10.1055/a-1468-5725
DOI: 10.1055/a-1468-5725
letter
Brønsted Acid Catalyzed Cyclization of Inert N-Substituted Pyrroles to Benzo[f]pyrrolo[1,2-a][1,4]diazepines
Financial support from the National Natural Science Foundation of China (21602231) and the Natural Science Foundation of Jiangsu Province (BK20191197 and BK20181373) is gratefully acknowledged.
Abstract
Two approaches involving intramolecular and intermolecular cyclization, respectively, have been developed for the direct and practical construction of a series of important benzo[f]pyrrolo[1,2-a][1,4]azepines by using Brønsted acid catalysts. Upon catalysis by TsOH, the intramolecular dehydroxylation/ring closure of 3-hydroxy-2-[2-(1H-pyrrol-1-yl)benzyl]isoindolin-1-ones provided various racemic benzo[f]pyrrolo[1,2-a][1,4]azepines in high yields. Furthermore, enantioenriched benzo[f]pyrrolo[1,2-a][1,4]azepines were also obtained by chiral phosphoric acid catalyzed intermolecular addition of [2-(1H-pyrrol-1-yl)phenyl]methanamines to 2-formylbenzoates under mild conditions.
Key words
Brønsted acid catalysis - cyclization - pyrroles - intermolecular addition - azepines - asymmetric catalysisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1468-5725.
- Supporting Information
Publikationsverlauf
Eingereicht: 14. Dezember 2020
Angenommen nach Revision: 27. März 2021
Accepted Manuscript online:
27. März 2021
Artikel online veröffentlicht:
16. April 2021
© 2021. Thieme. All rights reserved
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- 12 9H-Isoindolo[1,2-c]pyrrolo[1,2-a][1,4]benzodiazepin-11(15bH)-ones 2a–q; General Procedure (Intramolecular Reaction) The appropriate isoindolone 1 (0.2 mmol, 1.0 equiv) and TsOH (1 mol%) were stirred in CH2Cl2 (1 mL) at r.t. When the reaction was complete, the solvent was removed and the crude mixture was purified by flash column chromatography (silica gel, hexane–EtOAc). 9H-Isoindolo[1,2-c]pyrrolo[1,2-a][1,4]benzodiazepin-11(15bH)-ones 2a, 2q–t; General Procedure (Intermolecular Reaction) The appropriate amine 3 (0.1 mmol, 1.0 equiv), methyl 2-formylbenzoate (4a, 0.15 mmol, 1.5 equiv), chiral phosphoric acid A5 (5.0 mol%), and 4 Å MS (100 mg) were stirred in toluene (1.0 mL) at r.t. under N2. Upon completion of the reaction, the solvent was removed and the crude mixture was purified by flash column chromatography. 9H-Isoindolo[1,2-c]pyrrolo[1,2-a][1,4]benzodiazepin-11(15bH)-one (2a) White solid; yield: 53.2 mg (93%); mp 192-195 °C. 1H NMR (400 MHz, CDCl3): δ = 7.91 (d, J = 7.5 Hz, 1 H), 7.64–7.44 (m, 6 H), 7.35 (t, J = 7.4 Hz, 1 H), 7.10 (d, J = 2.9 Hz, 1 H), 6.26 (t, J = 3.3 Hz, 1 H), 5.94 (d, J = 3.5 Hz, 1 H), 5.40 (s, 1 H), 5.06 (d, J = 13.9 Hz, 1 H), 4.17 (d, J = 13.9 Hz, 1 H). 13C NMR (101 MHz, CDCl3): δ = 167.0, 141.7, 140.2, 133.6, 131.5, 131.2, 130.0, 128.9, 128.5, 127.3, 124.0, 123.6, 121.8, 109.5, 107.2, 56.4, 44.6. CCDC 1964245 contains the supplementary crystallographic data for compound 2a. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures.
For asymmetric addition of unprotected pyrroles, see: