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Synlett 2016; 27(08): 1241-1244
DOI: 10.1055/s-0035-1561559
DOI: 10.1055/s-0035-1561559
letter
Indium(III) Chloride Catalyzed Synthesis of 5-Substituted 1H-Tetrazoles from Oximes and Sodium Azide
Further Information
Publication History
Received: 24 November 2015
Accepted after revision: 30 December 2015
Publication Date:
27 January 2016 (online)
◊ Authors contributed equally.
Abstract
A simple and efficient protocol has been developed for the synthesis of 5-substituted 1H-tetrazole derivatives in good to excellent yields from various oximes and sodium azide by using indium(III) chloride as a Lewis acid catalyst. The present method has significant advantages, such as an inexpensive catalyst, low catalyst loading, mild reaction conditions, and simple experimental procedures.
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References and Notes
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- 22 5-Substituted 1H-Tetrazoles 2a–r: General Procedure InCl3 (3 mol%) was added to a stirred solution of the appropriate aldoxime (1 mmol) and NaN3 (1.5 mmol) in DMF (5 mL), and the mixture was heated to 120 °C. When the reaction was complete (TLC), the mixture was cooled to r.t., H2O (5 mL), 2 M aq HCl (10 mL), and EtOAc (10 mL) were successively added, and the mixture was stirred vigorously for 15 min. The organic layer was separated, and the aqueous layer was extracted with EtOAc (3 × 15 mL). The combined organic extracts were washed with H2O, dried (Na2SO4), and filtered. The solvent was evaporated under reduced pressure, and the crude product was purified by column chromatography [silica gel, EtOAc–hexane (9:1)]. 2-[4-(1H-Tetrazol-5-yl)phenoxy]acetohydrazide (2j) White solid; yield: 403 mg (72%); mp 197–199 °C. IR (KBr): 3432, 3318, 2869, 2645, 1614, 1521, 1450, 1280, 1172, 1108, 836 cm–1. 1H NMR (500 MHz, DMSO-d 6): δ = 9.36 (br s, 1 H), 7.92 (d, J = 8.8 Hz, 2 H), 7.00 (d, J = 8.8 Hz, 2 H), 4.49 (s, 2 H). 13C NMR (125 MHz, DMSO-d 6): δ = 166.6, 159.4, 157.4, 127.2, 124.3, 114.6, 66.2. HRMS: m/z [M + H]+ calcd for C9H11N6O2: 235.0938; found: 235.0939. 5-(4-Phenyl-2-thienyl)-1H-tetrazole (2p) White solid; yield: 466 mg (83%); mp 240–242 °C. IR (KBr): 3220, 2260, 1574, 1478, 1261, 1153, 1066, 886, 778 cm–1. 1H NMR (500 MHz, DMSO-d 6): δ = 8.21 (s, 1 H), 8.07 (s, 1 H), 7.74 (d, J = 7.2 Hz, 2 H), 7.68 (d, J = 7.2 Hz, 2 H) 7.45–7.33 (m, 1 H). 13C NMR (125 MHz, DMSO-d 6): δ = 162.7, 141.6, 140.8, 134.6, 128.9, 127.4, 127.2, 125.7, 125.6. HRMS: m/z [M + H]+ calcd for C11H9N4S: 229.0542; found: 229.0543.