Novel synthesis of naphthobenzazepines from N-bromobenzylnaphthylamines by regioselective C-H activation utilizing the intramolecular coordination of an amine to Pd

Synlett

Volumn , Issue 8, 2003, Pages 1141-1144

  Harayama, Takashi ^a   Sato, Tomonori ^a   Hori, Akihiro ^a   Abe, Hitoshi ^a   Takeuchi, Yasuo ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

C H activation; Heterocycles; Palladium; Regioselectivity; Synthetic methods

Indexed keywords

AMINE; BENZAZEPINE DERIVATIVE; BROMOBENZENE; N BROMOBENZYLNAPHTHYLAMINE DERIVATIVE; NAPHTHOBENZAZEPINE DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; MOLECULAR INTERACTION; QUANTUM YIELD; STEREOCHEMISTRY; SYNTHESIS;

EID: 0038391454     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-39911     Document Type: Article

References (31)

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20. 3): Compound 9a: δ = 3.01 (3 H, s, N-Me), 6.57 (1 H, br. d, J = 7.0 Hz), 6.86 (1 H, d, J = 8.5 Hz), 7.02 (1 H, s), 7.08 (1 H, br. d, J = 7.0 Hz), 7.14 (1 H, t, J = 7.0 Hz), 7.41 (1 H, d, J = 8.5 Hz). Compound 11a: δ = 2.75 (3 H, s, N-Me), 7.11 (1 H, s), 7.75 (1 H, s).
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23. BN), 6.84 (1 H, d, J = 8.8 Hz), 7.10 (1 H, dd, J = 7.6, 1.4 Hz), 7.17 (1 H, s), 7.29 (1 H, t, J = 7.8 Hz), 7.59 (1 H, d, J = 8.8 Hz), 7.61 (1 H, dd, J = 7.8, 1.4 Hz).
24. 17 in 86% and 76% yields, respectively, via trifluoroacetylation, methylation with MeI and hydrolysis with alkaline aqueous EtOH.
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26. 3): Compound 9b: δ = 3.05 (3 H, s, N-Me). Compound 9c: δ = 2.97 (3 H, s, N-Me), 7.06 (1 H, s). Compound 9d: δ = 3.08 (3 H, s, N-Me), 6.92 (1 H, d, J = 8.6 Hz), 7.14 (1 H, d, J = 8.6 Hz). Compound 9e: δ = 3.00 (3 H, s, N-Me), 6.88 (1 H, d, J = 8.6 Hz), 7.03 (1 H, s), 7.45 (1 H, d, J = 8.6 Hz). Compound 9f: δ = 2.98 (3 H, s, N-Me), 3.48 (3 H, s, OMe), 7.07 (1 H, s). Compound 9g: δ = 3.03 (3 H, s, N-Me), 3.48 (3 H, s, OMe), 6.85 (1 H, d, J = 8.8 Hz), 7.03 (1 H, s), 7.27 (1 H, d, J = 8.8 Hz).
27. 20 186-188°C). Compound 10h: δ = 2.63 (3 H, s, N-Me), 7.14 (1 H, s), 7.53 (1 H, d, J = 8.6 Hz), 7.69 (1 H, s), 7.78 (1 H, d, J = 8.6 Hz). Compound 10i: δ = 2.62 (3 H, s, N-Me), 6.94 (1 H, d, J = 8.4 Hz), 7.13 (1 H, s), 7.50 (1 H, d, J = 8.4 Hz), 7.51 (1 H, d, J = 8.6 Hz), 7.69 (1 H, s), 7.71 (1 H, d, J = 8.6 Hz).
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29. 3): Compound 11f: δ = 2.82 (3 H, s, N-Me), 7.04 (1 H, dd, J = 7.4, 1.2 Hz), 7.13 (1 H, s), 7.63 (1 H, s). Compound 11g: δ = 2.84 (3 H, s, N-Me), 6.86 (1 H, dd, J = 8.0, 1.4 Hz), 7.12 (1 H, s), 7.59 (1 H, s). Compound 11h: δ = 2.81 (3 H, s, N-Me), 7.02 (1 H, dd, J = 7.6, 1.2 Hz), 7.13 (1 H, s), 7.62 (1 H, s). Compound 11i: δ = 2.84 (3 H, s, N-Me), 6.87 (1 H, dd, J = 8.0, 1.2 Hz), 7.11 (1 H, s), 7.56 (1 H, s). Compound 12g: δ = 6.56 (1 H, br d, J = 7.2 Hz), 7.02 (1 H, s), 7.10 (1 H, s). Compound 12h: δ = 6.55 (1 H, dd, J = 7.0, 1.4 Hz), 7.12 (1 H, s), 7.18 (1 H, s). Compound 12i: δ = 6.60 (1 H, dd, J = 7.4, 1.2 Hz), 7.01 (1 H, s), 7.11 (1 H, s).
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