Facile Synthesis of Benzo[d]azol-2(3H)-ones Using 2-Phenoxycarbonyl-4,5-dichloropyridazin-3(2H)-one as Green CO Source

Abstract

Developing eco-friendly, stable, and easy-to-handle acyl sources is of great importance in synthetic and green chemistry. This study describes the synthesis of benzo[d]azol-2(3H)-ones such as benzo[d]thiazol-2(3H)-ones, benzo[d]oxazol-2(3H)-ones, and benzo[d]imidazol-2(3H)-ones using 2-phenoxycarbonyl-4,5-dichloropyridazin-3(2H)-one in one pot. The reaction reported is carried out under neutral or acidic conditions in the presence of zinc or sodium bicarbonate to give the corresponding heterocycles in good to excellent yields. The reaction uses a solid stable carbonyl source that is a recyclable functional-group carrier, pyridazin-3(2H)-one.

Key words

carbonylation - green chemistry - heterocycles - medicinal chemistry - ring closure

• References and Notes


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• 17 Synthesis of 3: General Procedure A mixture of 2-phenoxycarbonyl-4,5-dichloropyridazin-3(2H)-one (2a, 1.2 equiv), compounds (1, 1 equiv), and toluene (5 mL) was stirred at reflux conditions until 1 was consumed (monitored by TLC). After adding NaHCO₃ (1 equiv), the mixture was refluxed until the intermediate was consumed (monitored by TLC). After cooling to r.t., the resulting precipitate was filtered off and washed with THF. The solvent was evaporated under reduced pressure. The resulting residue was transferred to an open-bed silica gel column (3 × 10 cm). The column was eluted with n-hexane–THF (3:1, v/v). Fractions containing compounds 3 were combined and evaporated under reduced pressure to give compounds 3. Benzo[d]oxazol-2(3H)-one (3a) Yield: 340 mg (92%); white solid; mp 140 °C (lit.¹⁶ 141–142 °C). IR (KBr): 3215, 1772, 1733, 1480, 1398, 1307, 1253, 1147, 1009, 944, 739, 718, 701, 574 cm^–1. ¹H NMR (300 MHz, DMSO-d ₆): δ = 7.10–7.26 (m, 3 H), 9.87 (s, 1 H). ¹³C NMR (75 MHz, DMSO-d ₆): δ = 110.17, 110.25, 122.76, 124.23, 129.42, 143.90, 156.23. HRMS (m/z): [M]⁺ calcd for C₇H₅NO₂: 135.0320; found: 135.0319. See the Supporting Information for experimental details and characterization data for all compounds. Synthesis of 5: General Procedure A mixture of 2-phenoxycarbonyl-4,5-dichloropyridazin-3(2H)-one (2a, 1.2 equiv), compounds 4 (1 equiv), and toluene (10 mL) was stirred at reflux conditions until amide intermediate was consumed (monitored by TLC). After cooling to r.t., the resulting precipitate was filtered off and the solvent was evaporated under reduced pressure. The residue was transferred to an open-bed silica gel column (3 × 7 cm). The column was eluted with n-hexane–THF (1:2, v/v). Fractions containing compounds 5 were combined and evaporated under reduced pressure to give compounds 5. Benzo[d]imidazol-2(3H)-one (5a) Yield: 335 mg (90%); white solid; mp 320–322 °C (lit.⁹ 305–308 °C). IR (KBr): 3178, 3114, 3027, 2910, 2807, 2726, 1743, 1483, 1361, 1270, 1197, 1027, 736, 703, 597 cm^–1. ¹H NMR (300 MHz, DMSO-d ₆): δ = 6.91 (s, 4 H), 10.56 (s, 2 H). ¹³C NMR (75 MHz, DMSO-d ₆): δ = 108.42, 113.27, 120.49, 126.96, 129.63, 130.24, 155.28. HRMS: m/z [M]⁺ calcd for C₇H₆N₂O: 134.0480; found: 134.0480. Synthesis of 11 – General Procedure A mixture of 2-phenoxycarbonyl-4,5-dichloropyridazin-3(2H)-one (2a, 1.2 equiv), compounds 6 (1 equiv), and AcOH (5 mL) was stirred at r.t. (for 11a) or at reflux conditions (for 11b,c) until 6 was consumed (monitored by TLC). After adding zinc powder (5 equiv), the mixture was refluxed for 0.5 h. After cooling to r.t., the resulting precipitate was filtered off and washed with CH₂Cl₂ (for 11a) or THF (for 11b,c), the solvent was evaporated under reduced pressure. The resulting residue was transferred to an open-bed silica gel column (3 × 10 cm). The column was eluted with CH₂Cl₂–EtOAc (10:1, v/v). Fractions containing compounds 11 were combined and evaporated under reduced pressure to give compounds 11. Benzo[d]thiazol-2(3H)-one (11a) Yield: 341 mg (93%); light yellow solid; mp 138–139 °C (lit.^7a 139–141 °C). IR (KBr): 3307, 3154, 3108, 3054, 3946, 2881, 2823, 2740, 2674, 1680, 1592, 1463, 1413, 1214, 1222, 742, 701, 642 cm^–1. ¹H NMR (300 MHz, DMSO-d ₆): δ = 7.10–7.15 (m, 2 H), 7.26–7.31 (m, 1 H), 7.55–7.58 (m, 1 H), 11.89 (s, 1 H). ¹³C NMR (75 MHz, DMSO-d ₆): δ = 111.44, 122.56, 122.66, 123.23, 126.38, 136.27, 169.98. HRMS: m/z [M]⁺ calcd for C₇H₅NOS: 151.0092; found: 151.0091.