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Synlett 2022; 33(01): 70-75
DOI: 10.1055/a-1665-8562
DOI: 10.1055/a-1665-8562
letter
S8-Mediated Cyclization of Bis(2-aminophenyl) Disulfide/Diselenide with Arylacetylenes/Styrenes: Access to 2-(Arylmethyl)-1,3-benzothiazoles/benzoselenazoles
This work was supported by the National Key Research and Development Program of China (2019YFC1906603), the Jiangsu Synergetic Innovation Center for Advanced Bio-Manufacture (XTC1806), the National Natural Science Foundation of China (22078152), and the Six Talent Peaks Project in Jiangsu Province (SWYY-030/SWYY-118).
Abstract
A novel S8-mediated approach to benzothiazoles/benzoselenazoles from bis(2-aminophenyl) disulfides/diselenides and phenylacetylenes or styrenes has been developed. 2-(Arylmethyl)-1,3-benzoselenazoles were comprehensively synthesized for the first time. The reactions proceeded in moderate to excellent yields, and with a gram-scale application.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1665-8562.
- Supporting Information
- CIF File
Publication History
Received: 18 August 2021
Accepted after revision: 10 October 2021
Accepted Manuscript online:
10 October 2021
Article published online:
29 October 2021
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- 9 2-Benzyl-1,3-benzothiazole (3aa) and 2-Benzyl-1,3-benzoselenazole (7aa); Typical Procedures From ethynylbenzene: A mixture of ethynylbenzene (1a; 23 μL, 0.2 mmol), bis(2-aminophenyl) disulfide 2a (50 mg, 0.2 mmol) [or bis(2-aminophenyl) diselenide 6a (69 mg, 0.2 mmol)], elemental S (12.8 mg, 0.4 mmol), NaHCO3 (33.6 mg, 0.4 mmol), and DMF (or NMP) (0.6 mL) was placed in a sealed pressure vessel (10 mL) containing a magnetic stirring bar. The vessel was then capped and the mixture was stirred at 110 °C for 16 h under air (or at 130 °C for 24 h under N2) until the reaction was complete (TLC). The mixture was cooled to rt and treated with EtOAc (15 mL) and H2O (10 mL). The organic phase was then separated, washed with brine, dried, filtered, concentrated under vacuum, and purified by column chromatography [silica gel, PE–EtOAc (40:1 or 50:1)] to afford 3aa as a light-yellow oil (yield: 42 mg, 94%) [or 7aa as a light-yellow solid (yield: 46 mg, 85%)].From styrene: A mixture of styrene 4a (24 μL, 0.2 mmol), bis(2-aminophenyl) disulfide 2a (0.2 mmol), elemental S (12.8 mg, 0.4 mmol), NaHCO3 (33.6 mg, 0.4 mmol), and DMF (0.6 mL) was placed in a sealed pressure vessel (10 mL) containing a magnetic stirring bar. The vessel was then capped and the mixture was stirred at 110 °C for 16 h under air until the reaction was complete (TLC). Similar workup to the above gave 3aa as a light-yellow oil; yield: 42 mg (93%).From 2,2′-trisulfanediyldianiline: A mixture of ethynylbenzene (1a; 23 μL, 0.2 mmol), 2,2′-trisulfanediyldianiline (5a; 56 mg, 0.2 mmol), elemental S (12.8 mg, 0.4 mmol), NaHCO3 (33.6 mg, 0.4 mmol), and DMF (0.6 mL) was placed in a sealed pressure vessel (10 mL) containing a magnetic stirring bar. The vessel was then capped and the mixture was stirred at 110 °C for 16 h under air until the reaction was complete (TLC). Similar workup to the above gave 3aa as a light-yellow oil; yield: 36 mg (79%).2-Benzyl-1,3-benzothiazole (3aa)[CAS Reg. No. 6265-94-7]Light-yellow oil. 1H NMR (400 MHz, CDCl3): δ = 7.95 (d, J = 8.1 Hz, 1 H), 7.71 (d, J = 8.0 Hz, 1 H), 7.36–7.40 (m, 1 H), 7.23–7.33 (m, 6 H), 4.37 (s, 2 H). 13C NMR (100 MHz, CDCl3): δ = 171.1, 153.1, 137.1, 135.5, 129.0, 128.8, 127.2, 125.9, 124.7, 122.6, 121.4, 40.5.The spectral data agreed with those reported in the literature; see ref. 3c.2-Benzyl-1,3-benzoselenazole (7aa)[CAS Reg. No.854053-83-1]Light-yellow solid. 1H NMR (500 MHz, CDCl3): δ = 8.01 (d, J = 8.1 Hz, 1 H), 7.77 (d, J = 7.9 Hz, 1 H), 7.39–7.42 (m, 1 H), 7.31–7.35 (m, 4 H), 7.26–7.29 (m, 1 H), 7.21 (t, J = 7.6 Hz, 1 H), 4.36 (s, 2 H). 13C NMR (125 MHz, CDCl3): δ = 176.6, 154.8, 139.1, 137.5, 129.2, 128.8, 127.4, 125.9, 124.8, 124.7, 124.2, 43.7.