Diastereoselective synthesis of atropisomeric 3-(2-substituted aryl)quinazolin-4-ones and their stereochemical properties

Heterocycles

Volumn 70, Issue , 2006, Pages 93-99

  Tokitoh, Takashi ^a   Kobayashi, Toshitake ^a   Nakada, Eisuke ^a   Inoue, Tohru ^a   Yokoshima, Satoshi ^a   Takahashi, Hideyo ^b   Natsugarib, Hideaki ^b  

^a UNIVERSITY OF TOKYO   (Japan)

^b TEIKYO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33947680816     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-06-s(w)26     Document Type: Article

References (23)

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13. Since partial racemization at the amino acid moiety during the reaction, presumably at the step of 7 → 8, was observed in the preliminary experiments, racemic amino acids (5) (DL-alanine and DL-phenylalanine) were used in this study to avoid the complexity of the chemistry, and thus the compounds (5-9) are racemic, but only one enantiomer is depicted for convenience.
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21. 3) are as follows: 7.57 (t, J= 7.8 Hz, 114), 6.90 (d, J=7.2 Hz, 214), 6.31 (d, J= 7.8 Hz, 114), 4.51 (dd, J= 15.6, 8.4 Hz, 114), 3.68 (s, 314), 3.25 (dd, J= 19.2, 8.4 Hz, 114), 2.95 (broad, 114), 1.33 (s, 9x0.814), 1.07 (s, 9x0.214).
22. 1H COSY NMR using a mixture of 9R*-c and 9S*-c.
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