SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 12, 2008, Pages 1852-1856

Synthesis of new pyrrolobenzazepines via Pictet-Spengler cyclization

(4) Gracia, Stéphanie a Schulz, Jürgen a Pellet Rostaing, Stéphane a Lemaire, Marc a

a UNIVERSITÉ LYON 1 (France)

Author keywords

Azepine; Fused ring systems; Pictet Spengler reaction; Pyrrole

Indexed keywords

BENZAZEPINE DERIVATIVE; PYRROLE DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; PICTET SPENGLER REACTION;

EID: 48349088650 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1078567 Document Type: Article

Times cited : (16)

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- General Procedure for Preparation of Compounds 10-13 To a stirred 1 M solution of amine 6, 7, 8, or 9 in anhyd toluene was added the para-substituted benzaldehyde derivative (1.1 equiv, under argon atmosphere (in the case of amines 8 and 9, 4 equiv of MgSO 4 were added, The mixture was heated at reflux until total conversion of the amine into the intermediary imine (followed by 1H NMR, Then, the mixture was cooled to r.t. to add TFA (5 or 10 equiv, The resulting mixture was left at specified temperature (r.t. or 70°C) until completion of the reaction. Residual TFA was neutralized at 0°C with an aq sat. NaHCO3 solution. The reaction mixture was extracted with CH 2Cl2. The combined organic layers were successively washed with H2O and brine, dried over MgSO4, filtered, and solvents removed under reduced pressure. The crude product was purified by flash chromat
- 3): δ = 2.33 (s, 3 H), 3.63 (d, J = 16.2 Hz, 1 H), 3.73 (br s, 1 H), 4.14 (d, 16.2 Hz, 1 H), 6.06 (m, 1 H), 6.08 (dd, J = 1.3, 7.3 Hz, 1 H), 6.28 (d, J = 3.4 Hz, 1 H), 6.73 (d, J = 8.3 Hz, 2 H), 6.85 (m, 2 H), 6.97 (d, J = 8.3 Hz, 2 H), 7.04 (d, J = 8.3 Hz, 2 H), 7.11 (dd, J = 1.3, 7.1 Hz, 1 H), 7.15 (d, J = 8.3 Hz, 2 H), 7.30 (d, J = 3.4 Hz, 1 H). HRMS: m/z = 439.5326.

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- General Procedure for Preparation of Compounds 14-17 A mixture of the azepine 10a-e, 11a-e, 12a-e, or 13a-e (1 equiv) and TBAF 1 M solution in THF (10 equiv) was heated at 70°C for 10 h. The mixture was washed with H2O. The aqueous phase was extracted with CH 2Cl2. The combined organic layers were dried over MgSO4, filtered, and solvents removed under reduced pressure. The crude product was purified by flash chromatography. Analytical Data of Compound 15a Yellow solid obtained in 88% yield after flash chromatography (heptane-EtOAc, 8:2, 1H NMR (300 MHz, CDCl3, δ, 3.75 (s, 2 H, 6.21 (t, J, 2.6 Hz, 1 H, 6.93 (t, J, 2.6 Hz, 1 H, 7.2 (dd, J, 1.7, 6.6 Hz, 1 H, 7.22 (td, J, 1.7, 6.6 Hz, 1 H, 7.29 (td, J, 1.7, 6.6 Hz, 1 H, 7.48 (dd, J, 1.7, 7.2 Hz, 1 H, 7.76 (d, J, 8.3 Hz, 2 H, 8.0 (d, J, 8.3 Hz, 2 H, 8.24 br s, 1
- 3): δ = 32.6, 108.7, 114.1, 118.9, 123.3, 123.5, 126.9, 127.8, 128.2, 128.7, 130.5, 132.0, 132.8, 133.4, 144.2, 147.0, 155.0. HRMS: m/z = 437.5148.

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