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Synlett 2022; 33(07): 689-693
DOI: 10.1055/s-0041-1737338
DOI: 10.1055/s-0041-1737338
letter
1,4,2-Dioxazol-5-ones as Isocyanate Equivalents: Chemoselective Non-Metal-Catalyzed Carboxamidation of Indoles
Abstract
1,4,2-Dioxazol-5-ones are known to undergo decarboxylation under thermal conditions followed by Lossen’s rearrangement to give isocyanates. Described herein is the in situ trapping of the isocyanates by indoles to give indole-3-carboxamides in good to excellent yields.
Key words
dioxazolones - isocyanates - Lossen rearrangement - indolecarboxamides - metal-free reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0041-1737338.
- Supporting Information
Publikationsverlauf
Eingereicht: 07. Januar 2022
Angenommen nach Revision: 15. Januar 2022
Artikel online veröffentlicht:
03. Februar 2022
© 2022. Thieme. All rights reserved
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- 18 N-Phenyl-1H-indole-3-carboxamide (3aa); Typical Procedure KO t Bu (20 mmol) was added in one portion to a stirred solution of 1H-indole (2a; 10 mmol) and 3-phenyl-1,4,2-dioxazol-5-one (1a; 12 mmol) in toluene (20 mL) at r.t., and the mixture was then stirred at 110 °C for 1–2 h until the reaction was complete (TLC). The mixture was cooled to r.t. and H2O (20 mL) was then added. The resulting mixture was extracted with EtOAc (3 × 50 mL), and the extracts were dried (Na2SO4) and then concentrated under reduced pressure. The residue was purified by chromatography [silica gel, hexane–EtOAc (8:2)] to give a pale yellow solid; yield: 58 mg (57%); mp 172–174 °C. 1H NMR (400 MHz, DMSO-d 6): δ = 1.74 (br s, 1 H), 9.71 (br s, 1 H), 8.30 (d, J = 3.0 Hz, 1 H), 8.20 (d, J = 7.9 Hz, 1 H), 7.77 (d, J = 8.0 Hz, 2 H), 7.47 (d, J = 7.9 Hz, 1 H), 7.33 (t, J = 7.7 Hz, 2 H), 7.17 (m, 2 H), 7.04 (t, J = 7.4 Hz, 1 H). 13C NMR (100 MHz, DMSO-d 6): δ = 163.73, 140.30, 136.69, 129.13, 128.99, 126.90, 123.05, 122.59, 121.56, 121.11, 120.20, 112.41, 110.97. HRMS (ESI): m/z [M + H]+ calcd for C15H13N2O: 237.1028; found: 237.1026.