The use of tris(2-aminoethyl)amine in macrocyclization processes

Tetrahedron Letters

Volumn 39, Issue 22, 1998, Pages 3833-3836

  Lipkowski, Piotr ^a   Gryko, Daniel T ^a   Jurczak, Janusz ^a,b   Lipkowski, Janusz ^c  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

^b UNIVERSITY OF WARSAW   (Poland)

^c INSTITUTE OF PHYSICAL CHEMISTRY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; ESTER DERIVATIVE;

ARTICLE; COVALENT BOND; CRYSTAL STRUCTURE; CYCLIZATION; DIMERIZATION; SYNTHESIS; X RAY ANALYSIS;

EID: 0032575162     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00624-8     Document Type: Article

References (22)

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16. 16. Typical procedure: A mixture of tripodal amine (1 mmol) and tricarboxylate (1 mmol), dissolved in methanol (15ml), was left at room temperature for 30 days. The precipitated colorless crystals were recrystallized from a mixture of water, methanol and acetone, to afford pure crystalline product.
17. 2O): 36.2, 37.9, 50.6, 52.3, 60.3, 60.7, 172.5, 172.7.
18. 6): 34.8, 35.4, 35.9, 48.5, 50.6, 50.9, 51.5, 67.7, 71.7, 106.6, 107.4, 123.8, 135.9, 149.4, 150.6, 166.6, 167.5, 168.5.
19. 19. Typical procedure: A mixture of tris(2-aminoethyl)amine 1 (1 mmol) and dimethyl dicarboxylate 6 (2 mmol), dissolved in methanol (10 ml), was left at room temperature for 21 days. Then the reaction mixture was evaporated in vacuo, and the residue was subjected to high performance liquid chromatography (HPLC), using a preparative RP18 column and water-ethanol 95:5 v/v as an eluent to afford pure products 8 (11% yield) and 9 (4% yield).
20. 3): 3.32 (m, 12H), 3.68 (s, 3H), 3.94 (s, 4H), 4.02 (s, 2H), 4.23 (s, 2H), 7.71 (bs, 2H), 8.04 (bs, 1H).
21. 3): 36.0, 38.2, 51.2, 52.7, 70.4, 72.9, 168.8, 169.1.
22. 3): 35.9, 36.9, 51.5, 53.4, 67.4, 68.6, 113.1, 114.2, 122.3, 122.7, 146.4, 147.1, 167.6, 168.6.