Study on the Ring Eulargment Reaction: Synthesis of 7,8,13, 13a-tetrahydroisoindolo[1,2-b][3]benzazepine and 5,6,8,9,14,14a-hexahydroisoquino[1,2-b][3]benzazepine

Chinese Chemical Letters

Volumn 12, Issue 1, 2001, Pages 7-10

  Liu, Yu Xin ^a   Liang, Xiao Tian ^a  

^a INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

Isoindolo 1,2 b 3 benzazepines; Isoquino 1,2 b 3 benzazepines; Ring enlargement; Synthesis

Indexed keywords

EID: 0035579261     PISSN: 10018417     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (14)

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4. D. H. Kim, J.Heterocycl.Chem.,1992, 29, 11.
5. G. Rodriguez, M.M. Cid, Carlos Saa, L. Castedo and D. Dominguez, J.Org.Chem., 1996, 61, 2780.
6. J. H. Brewster and R.S. Jones, J.Org.Chem., 1969, 34, 354.
7. 1HNMR: 2.93 (dd, 1H, J=10.9, 14.5 Hz), 3.25 (dd, 1H, J=3.8, 15.0 Hz), 3.83∼4.01 (m, 15H), 4.11 (d, 1H, J= 14.0 Hz), 4.25 (d, 1H, J= 11.5 Hz), 6.64 (s, 1H), 6.71 (s, 1H), 6.78 (s, 1H), 6.82 (s, 1H).
8. 4, C 69.46 H 6.36, N 7.36; Found: C 69.20, H 6.18, N 7.43.
9. 1HNMR: 3.13∼3.21 (m, 3H), 3.45 (dd, 1H, J=9.6, 15.0 Hz), 3.70 (m, 1H), 3.79∼3.99 (m. 14H), 4.54 (d, 1H), 6.72 (s, 1H), 6.82 (m, 3H).
10. 13CNMR: 37.97, 41.44, 54.20, 55.52, 56.44, 56.48, 56.56, 56.70, 60.03, 69.64, 107.41, 107.83, 115.67; 115.96, 132.41, 134.30, 135.02, 137.10, 148.38, 149.83, 149.98.
11. D. Tourwe, G. Van Binst and T. Kametani, OMR, 1977, 9, 341.
12. 4: C 69.46, H 6.36, N 7.36; Found: C 69.20, H 6.18, N 7.43.
13. 3), 62.94 (CH), 97.48 (CH), 106.41 (CH), 110.20 (CH), 113.85 (CH), 114.17 (CH), 122.96 (C), 125.73 (C), 133.06 (C), 133.64 (C), 134.60 (C), 146.93 (C), 147.09 (C), 147.17 (C), 148.59 (C).
14. 1HNMR: 2.86∼3.53 (m, 9H), 3.66 (m, 1H), 3.83∼4.03 (m, 13H), 6.6∼6.8 (m, 4H).