Aqueous, One-Pot, Three-Component Reaction for Efficient Synthesis of 2-[4-(Arylsulfonyl)piperazin-1-yl]-1,3-benzothiazole, ‑1H-benzimidazole, or -1,3-benzoxazole Derivatives

Abstract

A simple and efficient synthetic protocol has been developed involving a one-pot three-component reaction of a 2-chlorobenzazole, piperazine, and an arenesulfonyl chloride under aqueous conditions at room temperature in the absence of a catalyst, ligand, or base. By using this protocol, a variety of 2-[4-(arylsulfonyl)piperazin-1-yl]-1,3-benzothiazole, -1H-benzimidazole, and -1,3-benzoxazole derivatives were synthesized in excellent yields.

Key words

chlorobenzazoles - piperazine - arenesulfonyl chlorides - benzothiazoles - benzoxazoles - benzimidazoles

• References and Notes

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• 35 2-[4-(Substituted arylsulfonyl)piperazin-1-yl]-1,3-benzothiazole, -1H-imidazole, and -1,3-oxazole Derivatives; General Procedure The appropriate arenesulfonyl chloride (1.0 mmol), piperazine (2.0 mmol), and 2-benzazole (1.0 mmol) were mixed in H₂O (3 mL), and the mixture was stirred at r.t for 2–3 h until the starting materials were completely consumed (TLC). The aqueous layer was then extracted with EtOAc (3 × 10 mL), and the organic layers were combined, washed with H₂O (30 mL) and sat. brine (30 mL), dried (Na₂SO₄), filtered, and concentrated under reduced pressure. The resulting crude product was washed with excess Et₂O and crystallized from EtOH. 2-[4-(Phenylsulfonyl)piperazin-1-yl]-1,3-benzoxazole (Table2, Entry 1) White solid; yield: 0.29 g (85%); mp 244–246 °C; ¹H NMR (500 MHz, CDCl₃): δ = 7.77 (dd, J = 5.3, 3.4 Hz, 2 H), 7.65 – 7.59 (m, 1 H), 7.54 (dd, J = 10.4, 4.7 Hz, 2 H), 7.33 (d, J = 8.0 Hz, 1 H), 7.23 (d, J = 8.0 Hz, 1 H), 7.16 (dd, J = 7.8, 1.1 Hz, 1 H), 7.03 (dd, J = 7.8, 1.1 Hz, 1 H), 3.81 (t, J = 5.1 Hz, 4 H), 3.16 (t, J = 5.1 Hz, 4 H). ¹³C NMR (126 MHz, CDCl₃): δ = 168.0, 152.3, 135.4, 133.2, 130.8, 129.3, 127.7, 126.2, 121.9, 120.8, 119.4, 47.8, 45.4. ESI-MS: m/z = 344 [M + H]⁺.