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Efficient, Iron-Catalyzed Synthesis of 2-Mercaptobenzothiazole Through S

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Efficient, Iron-Catalyzed Synthesis of 2-Mercaptobenzothiazole Through S Synthetic Communications An International Journal for Rapid Communication of Synthetic Organic Chemistry ISSN: 0039-7911 (Print) 1532-2432 (Online) Journal homepage: http://www.tandfonline.com/loi/lsyc20 Efficient, Iron-Catalyzed Synthesis of 2- Mercaptobenzothiazole Through S-Arylation/ Heterocyclization of 2-Haloaniline with Potassium Xanthate Min Gao, Chunqing Lou, Ning Zhu, Weijing Qin, Quanling Suo, Limin Han & Hailong Hong To cite this article: Min Gao, Chunqing Lou, Ning Zhu, Weijing Qin, Quanling Suo, Limin Han & Hailong Hong (2015) Efficient, Iron-Catalyzed Synthesis of 2-Mercaptobenzothiazole Through S-Arylation/Heterocyclization of 2-Haloaniline with Potassium Xanthate, Synthetic Communications, 45:20, 2378-2385, DOI: 10.1080/00397911.2015.1085573 To link to this article: http://dx.doi.org/10.1080/00397911.2015.1085573 View supplementary material Accepted online: 26 Aug 2015. Submit your article to this journal Article views: 6 View related articles View Crossmark data Full Terms & Conditions of access and use can be found at http://www.tandfonline.com/action/journalInformation?journalCode=lsyc20 Download by: [Inner Mongolia University of Technology] Date: 30 September 2015, At: 01:34 Synthetic Communications1, 45: 2378–2385, 2015 Copyright © Taylor & Francis Group, LLC ISSN: 0039-7911 print/1532-2432 online DOI: 10.1080/00397911.2015.1085573 EFFICIENT, IRON-CATALYZED SYNTHESIS OF 2-MERCAPTOBENZOTHIAZOLE THROUGH S-ARYLATION/HETEROCYCLIZATION OF 2- HALOANILINE WITH POTASSIUM XANTHATE Min Gao, Chunqing Lou, Ning Zhu, Weijing Qin, Quanling Suo, Limin Han, and Hailong Hong Chemical Engineering College, Inner Mongolia University of Technology, Hohhot, China GRAPHICAL ABSTRACT Abstract A mild and practical method for the synthesis of 2-mercaptobenzothiazole has been developed by using iron as an efficient catalyst. The present tandem reaction process allows access to a wide range of 2-mercaptobenzothiazoles in good to excellent yields by the reaction of 2-haloaniline with potassium O-ethyl dithiocarbonate in the 0 0 presence of FeF3 as a catalyst and 2,2 -bis(diphenylphosphino)-1,1 -binaphthyl as a ligand under an atmosphere of argon. Keywords 2-Haloaniline; iron-catalyzed synthesis; 2-mercaptobenzothiazole; tandem reaction INTRODUCTION Benzothiazole-containing compounds are common synthetic targets because of their interesting pharmaceutical and industrial applications. 2-Mercaptobenzothia- zoles (or 1,3-benzothiazole-2(3H)-thiones)[1,2] and 2-thio-substituted benzothiazoles, categorized as a derivative of benzothiazole, have been used as bioactive agents[3–6] Downloaded by [Inner Mongolia University of Technology] at 01:34 30 September 2015 and potential luminophores[7,8] (Fig. 1). For example, 6-methyl-2-mercaptoben- zothiazole 1 has been used as radioprotector to protect normal tissues adjacent to the tumor treated by radiotherapy,[3] and 2 might have the potential to be employed Received April 25, 2015. Address correspondence to Ning Zhu, Chemical Engineering College, Inner Mongolia University of Technology, Hohhot 010051, P. R. China. E-mail: [email protected] Color versions of one or more of the figures in the article can be found online at www.tandfonline. com/lsyc. 2378 SYNTHESIS OF 2-MERCAPTOBENZOTHIAZOLE 2379 Figure 1. Examples of 2-mercaptobenzothiazoles. as a new herbicide for weed control of wheat fields.[5] 2-Mercaptobenzothiazole derivatives 3 and 4 were evaluated for their potent antibacterial activity.[4] In addition, 2-mercaptobenzothiazole 5 can act not only as an accelerator of rubber vulcanization[2] but also as a significant ligand to form metallic complexes, which have promising luminescent properties.[7,8] Because of the importance of 2-mercaptobenzothiazole derivatives, an efficient synthesis of 2-mercaptobenzothia- zole under very mild reaction conditions has attracted much attention.[1,2,9–11] Conventionally, 2-mercaptobenzothiazole was prepared by the reaction of aniline with carbon disulfide under high pressure, which was used in the industrial production[12,13] (Scheme 1, route a). Though the starting material aniline was readily commercial available, the reaction was carried out under high pressure, and the harsh reaction conditions posed a serious threat to the manipulators. Furthermore, o-aminothiophenol reacted with carbon disulfide[14–18] or potassium=sodium O-ethyl dithiocarbonate[19] are usually used to produce 2-mercaptobenzothiazole (Scheme 1, route b). However, the starting material 2-aminobenzenethiols, especially those bearing additional substituents, were readily oxidized to stable disulfides and are not always easily available. Therefore, the disulfide, 2,20-disulfanediyldianiline, was used as starting material reacted with carbon disulfide in the presence of 1,8-diazabicyclo [5.4.0]undec-7-ene/ethanethiol (DBU/EtSH) to produce 2-mercaptobenzothiazole by our research group[9] (Scheme 1, route c). The odorous EtSH was used in this new Downloaded by [Inner Mongolia University of Technology] at 01:34 30 September 2015 Scheme 1. Strategies for the synthesis of 2-mercaptobenzothiazoles. 2380 M. GAO ET AL. synthetic method. An alternative approach to prepare 2-mercaptobenzothiazole used the DBU-promoted tandem reaction of 2-haloanilides with carbon disulfide[1,10] or nucleophilic aromatic substitution (SNAr) reaction of a potassium=sodium O-ethyl dithiocarbonate with 2-fluoroaniline, 2-chloroaniline, or 2-bromoaniline followed by a subsequent intramolacular cyclization[6,11,20–23] (Scheme 1, route d). However, the reaction of 2-iodoaniline with potassium=sodium O-ethyl dithiocarbonate could not afford the 2-mercaptobenzothiazole effectively in the present reaction conditions. Because of the cheap, efficient, nontoxic, and environmentally benign iron catalyst, the iron-catalyzed carbon-sulfur bond formation reactions have received [24] [25–29] [30] [31] [32,33] much attention. Recently, FeCl3, FeCl3 ·6H2O, FeCl2, FeF3, [34] [35] [36] Fe3O4, Fe(BF4)2, and Fe complexes had been used to catalyze cross-coupling and thia-Michael addition reactions for the formation of carbon–sulfur bonds. However, different reaction models needed different iron salts and ligands to make the reaction occur efficiently. Moreover, to the best of our knowledge, no report about the iron-catalyzed cross-coupling reaction of 2-haloaniline with potassium xanthate was found in the references. Herein we report a new facile and efficient FeF3-catalyzed tandem protocol for the synthesis of 2-mercaptobenzothiazole involving an S-arylation=intramolacular cyclization process. RESULTS AND DISCUSSION We began our study by examining the reaction of 2-iodoaniline (1a) with potass- ium O-ethyl dithiocarbonate (2) in dimethylformamide (DMF) by using different iron catalysts and ligands under various reaction conditions. Under the protection of an inert atmosphere, when 2-iodoaniline reacted with 3 equiv of potassium O-ethyl dithiocarbonate in the absence of any catalysts and ligands at 90 °C, only 15% yields of desired products were obtained as determined by mass spectrometry (MS) and NMR methods (Table 1, entry 1). Then various iron catalysts (10 mol%) were inves- tigated for this reaction under similar conditions. The use of anhydrous FeCl3, FeCl3 · 6H2O, and FeF3 all gave the desired product in moderate yield, and the results indi- cated that iron can play a catalytic role in this reaction (entries 2–4). Encouraged by these results, various nitrogen and phosphine ligands[26,28] (20 mol%) were sub- sequently evaluated under the catalysis of FeCl3 ·6H2O (entries 5–10). Among the various ligands examined, 2,20-bis(diphenylphosphino)-1,10-binaphthyl (L1) was the most effective ligand. However, the individual L1 ligand was ineffective in this reac- tion system (entry 11), which showed that L1 ligand and FeCl3 ·6H2O cocatalyzed the reaction of 1a and 2 to form 2-mercaptobenzothiazoles 3a in 73% yield. Furthermore, when FeF3 was used as the cocatalyst, the yield of 3a was increased to 83% (entry 12). Downloaded by [Inner Mongolia University of Technology] at 01:34 30 September 2015 When the reaction temperature was improved to 110 °C, the yield of corresponding product increased to 91% (entry 13), which indicated that the reaction temperature was another important factor for the yield of the product. After optimization of the ratio of the catalyst to ligand and other reaction conditions, it turned out that 5 mol% L1 ligand combined with 10 mol% FeF3 under 110 °C could provide the best results (entries 14–16). Bolm and Buchwald reported that trace amounts of copper impurities in iron catalyst could efficiently catalyze heteroatom to form C-S, C-O, and C-N in organic synthesis.[37] To verify that iron could catalyze the reaction of 2-iodoaniline with SYNTHESIS OF 2-MERCAPTOBENZOTHIAZOLE 2381 Table 1. Optimization of the reaction conditionsa Entry Catalyst Ligand Temp. (°C) Yieldb (%) 1 ——90 15 2 FeCl3 ·6H2O — 90 35 3 FeCl3 — 90 22 4 FeF3 — 90 41 5 FeCl3 ·6H2O L-Proline 90 41 0 6 FeCl3 ·6H2O 2,2 -Bipyridine 90 43 7 FeCl3 ·6H2O Dppe 90 31 8 FeCl3 ·6H2O Dppp 90 23 9 FeCl3 ·6H2OL2 90 19 10 FeCl3 ·6H2OL1 90 73 11 — L1 90 16 12 FeF3 L1 90 83 13 FeF3 L1 110 91 14 FeF3 L1 (10 mol%) 110 90 15 FeF3 L1 (5 mol%) 110 97 16 FeF3 L1 (1 mol%) 110 32 aConditions: 1a (0.6 mmol), 2 (1.8 mmol), catalyst (10 mol %), ligand (20 mol %), 4 mL DMF, 6 h, under an atmosphere of argon. bIsolated yield based on 1a. potassium O-ethyl dithiocarbonate in our reaction system, the high-purity FeCl3 (>99.99%) was used as catalyst under the optimized reaction conditions. The experimental result showed that the aim product was obtained in 80% yield, which indicated that the iron was a true catalyst in this coupling reaction system. Having optimized the reaction conditions through the use of FeF3 as catalyst and L1 as ligand, we explored the scope and limitations of this tandem reaction Downloaded by [Inner Mongolia University of Technology] at 01:34 30 September 2015 system, and the results are summarized in Table 2. When a variety of 2-haloaniline reactions with potassium O-ethyl dithiocarbonate were examined, the results demon- strated that 2-I, 2-Br, or 2-Cl substituted aniline could produce the product 3a in excellent yield (Table 2, entries 1–3).
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