Solid-phase synthesis of 2,3,5-trisubstituted 4H-imidazolones

Tetrahedron Letters

Volumn 43, Issue 38, 2002, Pages 6857-6860

  Lange, Udo E W ^a,b  

^a BASF SE   (Germany)

^b ABBOTT GMBH AND CO KG   (Germany)

Author keywords

4H imidazolones; Atropo isomers; Combinatorial chemistry; Solid phase synthesis

Indexed keywords

IMIDAZOLE DERIVATIVE;

ARTICLE; DEHYDRATION; DIASTEREOISOMER; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID; TECHNIQUE;

EID: 0037119684     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01400-4     Document Type: Article

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13. For biological activity of sulphur and organo-sulphur compounds, see: (a) The Pesticide Manual, 10th ed.; Tomlin, C., Ed.; The British Crop Protection Council and The Royal Society of Chemistry, The Bath Press: Bath, 1994; pp. 934-935; (b) Green, M. B.; Hartley, G. S.; West, T. F. Sulphur, organosulphur and other organic fungicides. In Chemicals for Crop Improvement and Pest Management, 3rd edition; Pergamon Press: Oxford, 1987; Chapter 16, pp. 167-173. For biological activity of mercuric salts, see: The Pesticide Manual, 10th ed.; Tomlin, C., Ed.; The British Crop Protection Council and The Royal Society of Chemistry, The Bath Press: Bath, 1994; pp. 657-659.
14. For biological activity of sulphur and organo-sulphur compounds, see: (a) The Pesticide Manual, 10th ed.; Tomlin, C., Ed.; The British Crop Protection Council and The Royal Society of Chemistry, The Bath Press: Bath, 1994; pp. 934-935; (b) Green, M. B.; Hartley, G. S.; West, T. F. Sulphur, organosulphur and other organic fungicides. In Chemicals for Crop Improvement and Pest Management, 3rd edition; Pergamon Press: Oxford, 1987; Chapter 16, pp. 167-173. For biological activity of mercuric salts, see: The Pesticide Manual, 10th ed.; Tomlin, C., Ed.; The British Crop Protection Council and The Royal Society of Chemistry, The Bath Press: Bath, 1994; pp. 657-659.
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24. Unpublished results; for a discussion on the formation of regioisomers cf. Ref. 3e.
25. Representative procedure: Merrifield resin bound phenylalanine (loading 0.8 mmol/g, 290 mg, 0.23 mmol) was reacted with 2-chlorophenylisocyanate (138 mg, 0.9 mmol) at room temperature in dichloromethane (DCM, 5.8 mL) for 12 h. After washing (4×DCM) the urea was dehydrated with Burgess reagent (164 mg, 0.69 mmol) in DCM (5.8 mL) at room temperature for 12 h. After washing (2×DCM, 3×NMP, 3×DCM) the carbodiimide was reacted with N-phenylpiperazine (22.4 mg, 0.138 mmol) in DCM (5.8 mL) at room temperature for 12 h. Filtration and concentration in vacuo gave the desired 5-benzyl-3-(2-chlorophenyl)-2-(N′-phenyl-N-piperazinyl)-4H-imidazolone (yield: 48 mg, 0.108 mmol, 78%, 90% purity by RP-HPLC at 214 nm).
26. The library synthesis was performed on a Bohdan automated synthesizer.