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Synlett 2017; 28(17): 2295-2298
DOI: 10.1055/s-0036-1590972
DOI: 10.1055/s-0036-1590972
letter
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
K.D. thanks the Council of Scientific and Industrial Research (CSIR), New Delhi, for financial assistance through the 12th Five Year plan projects “Affordable Cancer Therapeutics (ACT)’’ (CSC 0301) and “Small Molecules in Lead Exploration (SMiLE)” (CSC0111)Further Information
Publication History
Received: 14 May 2017
Accepted after revision: 28 June 2017
Publication Date:
03 August 2017 (online)
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 - benzimidazolesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1590972.
- Supporting Information
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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]+.