메뉴 건너뛰기
Synlett
Volumn , Issue 4, 2008, Pages 583-585
Chalcones to functionalized azetidines via anion-induced cyclization using task-specific ionic liquids
Author keywords

Azetidines; Chalcones; Ionic liquids; Michael addition; Phosphoramidates
Indexed keywords

ANION; AZETIDINE DERIVATIVE; CHALCONE DERIVATIVE; IONIC LIQUID; PHOSPHORAMIDIC ACID DERIVATIVE;
EID: 40949088199     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1042757     Document Type: Article
Times cited : (26)
References (40)
  • 39
    • 40949091091 scopus 로고    scopus 로고
    • General Procedure for the Synthesis of Diethyl N-Aryl-N-(1,3-diaryl-3-oxopropyl)phosphoramidates 325 To a solution of diethyl N-arylphosphoramidate 2 (5 mmol) in dry benzene (5 mL) was added dropwise a solution of NaH (120 mg, 5 mmol) in dry benzene (10 mL) with stirring at r.t. After the addition was complete and evolution of hydrogen gas(effervescence) had ceased, the reaction mixture was stirred at 60°C for 30 min and then cooled to r.t. Next, a solution of chalcone 1 (5 mmol) in dry benzene (5 mL) was added and the reaction mixture was stirred at 50-60°C for 3 h. The solvent was evaporated under reduced pressure, the residue washed with H2O and recrystallized from n-hexane to afford an analytically pure sample of 3. Physical Data of a Representative Compound Compound 3a: white crystals yield 87, mp 186-187°CIR KBr, νmax, 3052, 2990, 1692, 1605, 1582
    • 4P: C, 68.64; H, 6.45; N, 3.20. Found: C, 68.92; H, 6.74; N, 3.07.
  • 40
    • 40949103180 scopus 로고    scopus 로고
    • General Procedure for the Synthesis of Functionalized Azetidines 5 A mixture of adduct 3 (5 mmol) and [bmim]SCN or [bmim]SPh (4, 7.5 mmol) with a few drops of distilled H2O was taken in a 50 mL round-bottomed flask and stirred for 3-4 h at r.t, for [bmim]SCN) or at 60-65°C (for [bmim]SPh, After completion of the reaction as indicated by TLC, the product was extracted with Et2O (3 x 20 mL, dried over anhyd MgSO4, filtered, and evaporated to dryness. The crude product 5 thus obtained was recrystallized twice from n-hexane to afford an analytically pure sample. Physical Data of Representative Compounds Compound 5a: white crystals, yield 81, mp 98-99°C. IR (KBr, νmax, 3082, 2965, 2892, 2813, 2132, 1604, 1495, 1451, 753, 706 cm-1. 1H NMR (400 MHz, CDCl3/TMS, δ, 2.75 (dd, 1 H, J, 11.3, 8.7 Hz, 3-Ha, 3.05 dd, 1 H, J
    • 23NS: C, 82.40; H, 5.89; N, 3.56. Found: C, 82.76; H, 5.52; N, 3.85.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.