Regioselective introduction of homoallylic amine moiety to quinolines: Preparation of reissert compound followed by in-mediated allylation of nitrile

Bulletin of the Korean Chemical Society

Volumn 31, Issue 12, 2010, Pages 3822-3825

  Kim, Sung Hwan ^a   Lee, Sangku ^b   Kim, Yu Mi ^a   Kim, Jae Nyoung ^a  

^a Chonnam National University   (South Korea)

^b Korea Research Institute of Bioscience and Biotechnology (KRIBB)   (South Korea)

Author keywords

Allylation; Homoallylic amine; Indium; Quinolines; Reissert compounds

Indexed keywords

EID: 78650317178     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2010.31.12.3822     Document Type: Article

References (41)

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41. Deprotection of N-benzoyl group of 3a was easily conducted in aqueous EtOH in the presence of conc-HCl (reflux, 10 h) in 86%, and the spectroscopic data are as follows: pale yellow oil; IR (film) 3407, 3358, 1618, 1599, 1503, 1379 cm-1; 1H NMR (CDCh3, 300 MHz) † 2.46-2.56 (m, 1H), 2.64-2.73 (m, 1H), 3.40 (s, 2H), 4.31 (dd, J = 7.8 and 5.4 Hz, 1H), 5.06-5.16 (m, 2H), 5.71-5.85 (m, 1H), 7.42 (d, J = 8.1 Hz, 1H), 7.49 (ddd, J = 8.1, 6.9 and 1.2 Hz, 1H), 7.67 (ddd, J = 8.4, 6.9 and 1.5 Hz, 1H), 7.77 (dd, J = 8.1 and 1.2 Hz, 1H), 8.05 (d, J = 8.4 Hz, 1H), 8.08 (d, J = 8.4 Hz, 1H); ESIMS m/z 199 (M++H).