CuBr-Catalyzed One-Pot Three-Component Synthesis of Novel 2-(Carbazolyl)benzothiazoles

Abstract

A facile synthesis of various 2-(carbazolyl)benzothiazoles has been developed by one-pot CuBr-catalyzed three-component reactions of 2-iodoanilines, arylaldehydes, and elemental sulfur. Unlike traditional approach, this reaction exhibited a good functional group tolerance to produce the corresponding 2-(carbazolyl)benzothiazoles in good yields in the absence of any additive.

Key words

2-(carbazolyl)benzothiazoles - 2-iodoanilines - arylaldehydes - elemental sulfur

Publication History

Received: 10 August 2020

Accepted after revision: 21 August 2020

Article published online:
12 October 2020

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• 17 Representative Procedure A mixture of 9-ethyl-carbazole-3-carboxyaldehyde (1 mmol, 1 equiv), 2-iodoaniline (1.2 mmol, 1.2 equiv), sulfur powder (1.2 mmol, 1.2 equiv), and CuBr (0.2 mmol, 0.2 equiv) in DMF (5 mL) was stirred at 130 °C for 12 h. After completion of reaction (TLC monitoring), the reaction mixture was cooled to room temperature and extracted with ethyl acetate (2 × 20 mL). The combined organic extracts were dried over anhydrous Na₂SO₄, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to afford pure product 3a; yield 74%; white solid; mp 222–224 °C. ¹H NMR (400 MHz, CDCl₃): δ = 8.78 (d, J = 1.5 Hz, 1 H), 8.14–8.12 (m, 2 H), 8.00 (d, J = 8.0 Hz, 1 H), 7.83 (d, J = 8.0 Hz, 1 H), 7.46–7.35 (m, 4 H), 7.28 (t, J = 7.3 Hz, 1 H), 7.22 (t, J = 7.0, 1 H), 4.33 (q, J = 7.2 Hz, 2 H), 1.40 (t, J = 7.0 Hz, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 168.4, 153.4, 140.6, 139.6, 133.9, 125.4, 125.2, 124.5, 123.7, 123.6, 122.4, 122.0, 121.6, 120.5, 119.9, 119.1, 118.7, 107.9, 107.7, 36.8, 12.8. MS: m/z = 238.
• 18 CCDC 1950982 contains the supplementary crystallographic data for compound 3b. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures. Compound 3b: Formula: C₂₁H₁₅FN₂S, unit cell parameters: a = 11.9941(12), b = 32.955(5), c = 8.6385(8), space group Pccn. Final R factors R1 = 0.0503 and wR2 =0.1638; 227 parameters, 0 restraints, maximal residual electron density is 0.47 eÅ^–3.