TDAE-Initiated Synthesis of Oxiranes in Heterocyclic Series: Reaction of 2-(Dibromomethyl)quinoxaline with α -Dicarbonyl Derivatives

Letters in Organic Chemistry

Volumn 7, Issue 6, 2010, Pages 453-456

  Montana, Marc ^a   Terme, Thierry ^a   Vanelle, Patrice ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

dicarbonyl; Oxiranes; Quinoxaline; TDAE

Indexed keywords

EID: 78650372738     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017810791824801     Document Type: Article

References (38)

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33. General procedure for the reaction of 2-(dibromomethyl)quinoxaline 2 and ketone 3a or β-dicarbonyl derivatives 3b-f, using TDAE. Into a two-necked flask equipped with a silica-gel drying tube and a nitrogen inlet was added, under nitrogen at -20°C, 10 mL of anhydrous DMF solution of 2-(dibromomethyl)quinoxaline 2 (0.45 g, 1.5 mmol) and ketone 3a or β-dicarbonyl derivatives 3b-f, (4.5 mmol, 3 equiv.). The solution was stirred and maintained at this temperature for 30 min and then was added dropwise (via a syringe) the TDAE (0.3 g, 1.5 mmol). A red color immediately developed with the formation of a white fine precipitate. The solution was vigorously stirred at -20°C for 1 h and then warmed up to room temperature for 2 h. After this time TLC analysis (dichloromethane) clearly showed that compound 2 was totally consumed. The orange-red turbid solution was filtered (to remove the octamethyl-oxamidinium dibromide) and hydrolyzed with 80 mL of H2O. The aqueous solution was extracted with chloroform (3x40 mL) and the combined organic layers were washed with H2O (3x40 mL) and dried over MgSO4. Evaporation of the solvent left an orange oil as crude product. Purification by silica gel chromatography (dichloromethane) and recrystallization from ethanol gave the corresponding oxirane derivatives. New derivatives: 4a, like isomer, pink solid, mp 186°C, 1H NMR (CDCl3) Δ 1.65 (s, 3H, CH3); 4.25 (s, 1H, CH); 7.67 (d, J = 8.8 Hz, 2H, 2xCH); 7.83 (m, 2H, 2xCH); 8.11 (m, 2H, 2xCH); 8.27 (d, J = 8.8 Hz, 2H, 2xCH); 8.99 (s, 1H, CH). 13C NMR (CDCl3) Δ 17.0 (CH3); 63.1 (C); 66.0 (CH); 123.8 (2xCH); 126.4 (2xCH); 129.0 (CH); 129.5 (CH); 130.3 (CH); 130.7 (CH); 141.7 (C); 142.3 (C); 143.2 (CH); 147.6 (C); 148.2 (C); 149.8 (C). 4a, unlike isomer, pink solid, mp 157°C, 1H NMR (CDCl3) Δ 1.92 (s, 3H, CH3); 4.56 (s, 1H, CH); 7.49 (d, J = 8.8 Hz, 2H, 2xCH); 7.74 (m, 2H, 2xCH); 7.98 (m, 2H, 2xCH); 8.03 (d, J = 8.8 Hz, 2H, 2xCH); 8.39 (s, 1H, CH). 13C NMR (CDCl3) Δ 25.0 (CH3); 64.7 (CH); 65.9 (C); 123.6 (2xCH); 127.8 (2xCH); 128.7 (CH); 129.4 (CH); 130.1 (CH); 130.5 (CH); 141.4 (C); 141.9 (C); 142.4 (CH); 144.5 (C); 147.4 (C); 149.8 (C). Anal. Calcd for C17H13N3O3 (307.30): C, 66.44; H, 4.26; N, 13.67. Found: C, 65.65; H, 4.23; N, 13.51. 4b, trans isomer, white solid, mp 105°C, 1H NMR (CDCl3) Δ 1.34 (t, J = 7.2 Hz, 3H, CH3); 3.90 (d, J = 1.8 Hz, 1H, CH); 4.31 (q, J = 7.2 Hz, 2H, CH2); 4.47 (d, J = 1.8 Hz, 1H, CH); 7.80 (m, 2H, CH2); 8.10 (m, 2H, CH2); 8.79 (s, 1H, CH). 13C NMR (CDCl3) Δ 14.1 (CH3); 55.6 (CH); 57.0 (CH); 62.1 (CH2); 129.1 (CH); 129.4 (CH); 130.5 (CH); 130.8 (CH); 141.7 (C); 142.1 (C); 142.7 (CH); 149.4 (C); 167.1 (C=O). Anal. Calcd for C13H12N2O3 (244.25): C, 63.93; H, 4.95; N, 11.47. Found: C, 63.89; H, 4.96; N, 11.38. 4c, like isomer, pink oil, 1H NMR (CDCl3) Δ 1.45 (t, J = 7.1 Hz, 3H, CH3); 1.83 (s, 3H, CH3); 3.95 (q, J = 7.1 Hz, 2H, CH2); 4.32 (s, 1H, CH); 7.78 (m, 2H, CH2); 8.12 (m, 2H, CH2); 8.89 (s, 1H, CH). 13C NMR (CDCl3)Δ 13.0 (CH3); 19.4 (CH3); 60.6 (C); 62.2 (CH2); 63.2 (CH); 128.8 (CH); 129.3 (CH); 130.1 (CH); 130.3 (CH); 142.0 (C); 142.3 (C); 143.8 (CH); 149.2 (C); 167.9 (C=O). 4c, unlike isomer, pink oil, 1H NMR (CDCl3) Δ 0.95 (t, J = 7.1 Hz, 3H, CH3); 1.35 (s, 3H, CH3); 4.27 (q, J = 7.1 Hz, 2H, CH2); 4.64 (s, 1H, CH); 7.78 (m, 2H, CH2); 8.12 (m, 2H, CH2); 9.01 (s, 1H, CH). 13C NMR (CDCl3) Δ 13.7 (CH3); 14.1 (CH3); 60.6 (C); 61.4 (CH); 61.6 (CH2); 128.9 (CH); 129.4 (CH); 130.4 (CH); 130.7 (CH); 143.1 (CH); 141.2 (C); 141.6 (C); 149.2 (C); 169.5 (C). Anal. Calcd for C14H14N2O3 (258.27): C, 65.11; H, 5.46; N, 10.85. Found C, 63.80; H, 6.90; N, 7.53. 4d, red oil, 1H NMR (CDCl3) Δ 1.04 (t, J = 7.2 Hz, 3H, CH3); 1.36 (t, J = 7.2 Hz, 3H, CH3); 4.12 (q, J = 7.2 Hz, 2H, CH2); 4.36 (q, J = 7.2 Hz, 2H, CH2); 4.84 (s, 1H, CH); 7.81 (m, 2H, 2xCH); 8.09 (m, 2H, 2xCH); 8.86 (s, 1H, CH). 13C NMR (CDCl3) Δ 13.7 (CH3); 13.9 (CH3); 61.1 (CH); 62.3 (CH2); 62.4 (C); 63.2 (CH2); 129.2 (CH); 129.4 (CH); 130.7 (CH); 130.8 (CH); 141.6 (C); 142.5 (C); 142.6 (CH); 147.4 (C); 163.1 (C=O); 164.7 (C=O). Anal. Calcd for C16H16N2O5 (316.31): C, 60.7; H, 5.10; N, 8.86. Found: C, 60.01; H, 5.86; N, 7.96. 4e unlike, pink solid, mp 217°C, 1H NMR (CDCl3) Δ 3.13 (s, 3H, CH3); 4.97 (s, 1H, CH); 6.91 (d, J = 7.7 Hz, 1H, CH); 7.16 (m, 1H, CH); 7.30 (s, 1H, CH); 7;44 (m, 1H, CH); 7.76 (m, 2H, 2xCH); 7.98 (m, 1H, CH); 8.17 (m, 1H, CH); 9.42 (s, 1H, CH).
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