Stereoselective synthesis of bis-β-lactam grafted macrocycles

Tetrahedron Letters

Volumn 47, Issue 50, 2006, Pages 8855-8857

  Arumugam, Natarajan ^a   Raghunathan, Raghavachary ^a  

^a UNIVERSITY OF MADRAS   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM DERIVATIVE; MACROCYCLIC COMPOUND;

ARTICLE; CYCLOADDITION; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 33750619891     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.10.076     Document Type: Article

References (25)

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20. Representative experimental procedure for compound 2aA mixture of freshly distilled salicylaldehyde (2 mmol), m-xylene dibromide (1 mmol), anhydrous potassium carbonate (2 mmol) and dry acetone (20 ml) was stirred for 3 h at room temperature. The reaction mixture was then washed with water and extracted with chloroform. The organic layer was concentrated by distillation under reduced pressure to give the required dialdehyde in an excellent yield.
21. Representative experimental procedure for compound 3aA mixture of dialdehyde (1 mmol), ethylene diamine (1 mmol) and ethanol (100 ml) was stirred for 12 h at room temperature. After completion of the reaction the solvent was removed under reduced pressure to give the required bis-imine.
22. 4. The removal of the solvent by distillation under reduced pressure gave the crude product as a diastereomeric mixture. The diastereomers were separated by column chromatography (hexane:ethyl acetate 7:3) to give pure β-lactam in a good yield. The product was recrystallized from ethyl acetate.
23. 6: C, 75.21; H, 5.32; N, 4.38. Found: C, 75.22; H, 5.30; N, 4.40.
24. 6: C, 75.21; H, 5.32; N, 4.38. Found: C, 75.24; H, 5.30; N, 4.39.
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