A convenient and efficient route for the synthesis of amidecrownophanes via 1:1 macrocyclization of di(acid chloride) with diamine derivatives

Tetrahedron Letters

Volumn 48, Issue 17, 2007, Pages 3073-3076

  Gong, Wei Tao ^a   Hiratani, Kazuhisa ^a   Oba, Toru ^a   Ito, Satoshi ^a  

^a UTSUNOMIYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMIDECROWNOPHANE; CARBONYL DERIVATIVE; DIAMINE DERIVATIVE; DICARBONYL DICHLORIDE; MACROCYCLIC COMPOUND; UNCLASSIFIED DRUG;

AMIDATION; ARTICLE; CLAISEN REARRANGEMENT; HYDROGEN BOND; SYNTHESIS;

EID: 33947572340     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.02.097     Document Type: Article

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23. 2O), C, 69.68 (69.55); H, 6.72 (6.65); N, 4.29 (4.51).
24. 2O), C, 69.77 (69.55); H, 6.76 (6.65); N, 4.31 (4.51).
25. The preparation of 2b and 3b has already been reported under the high dilution method (yields: 2b 32%; 3b 82%). Yoshida H., Saigo K., and Hiratani K. Chem. Lett. (2000) 116-117
26. It was reported macrocycle that 2:2 macrocyclization occurred in the reaction of di(acid chloride) with p-phenylene diamine under the normal conditions. In that case, it was also presumed that hydrogen bonding in the noncyclic intermediate might play an important role to form 2:2 macrocycle. Numata M., Hiratani K., Nagawa Y., Houjou H., Masubuchi S., and Akabori S. New J. Chem. 26 (2002) 503-507
27. 2-), 7.28 (s, 2H, naphthyl), 7.40 (dd, J = 5 Hz, 2H, naphthyl), 7.53 (dd, J = 5 Hz, 2H, naphthyl), 7.86 (d, J = 8 Hz, 2H, naphthyl), 7.94 (d, J = 8 Hz, 2H, naphthyl), 8.17 (br, 2H, NH), 8.18 (s, 2H, naphthyl) ppm.