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Volumn , Issue 12, 2008, Pages 1773-1776

One-step synthesis of [1,2]diazepino[4,5-b]indole derivatives from the reaction of pyranoindolones with methylhydrazine

Author keywords

Bisnucleophiles; Diazepinoindoles; Methylhydrazine; Pyranoindolones

Indexed keywords

[1,2]DIAZEPINO[4,5, B]INDOLE DERIVATIVE; INDOLE DERIVATIVE; METHYLHYDRAZINE; PYRAINDOLONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPY; SYNTHESIS;

EID: 48349137011 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1078511 Document Type: Article

Times cited : (8)

References (20)

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18
- 48349108112
- All melting points were determined on a Büchi apparatus and are uncorrected. The 1H NMR and 13C NMR spectra were recorded on a Bruker AM300 spectrometer in CDCl3 with TMS as internal standard. All coupling constants are given in Hz and chemical shifts are given in ppm. Typical Experimental Procedure for the Preparation of 4e: To a stirred and refluxing solution of pyranoindolone 3e (1.5 mmol) in bromobenzene (15 mL, methylhydrazine (Fluka, purum; 3.0 mmol) was added and refluxing was continued for 20 min. The solvent was distilled off under reduced pressure to yield the corresponding crude product, which was purified by silica gel chromatography using petroleum ether-EtOAc (5:1) as eluent, to give 1-ethyl-3,10-dimethyl-5,10-dihydro[1,2]diazepino[4,5-b]indol-4(3H, one (4e, Yield: 73, yellow crystals; mp 104-106°C (ethanol, IR (nujol, 1651 cm-1. 1H NMR: δ, 1.16 t, J, 7
- 3O (255.31): C, 70.56; H, 6.71; N, 16.46. Found: C, 70.76; H, 6.83; N, 16.68.

19
- 48349106426
- Selected data for compound 5d. 1H NMR: δ, 2.27 (s, 3 H, 1′-Me, 3.16 (s, 3 H, 3′-Me, 3.73 (s, 3 H, 1-Me, 3.77 (s, 2 H, 3-CH2, 7.16 (ddd, J, 0.9, 7.1, 7.95 Hz, 1 H, C-5),14 7.27 (ddd, J, 1.2, 7.1, 8.2 Hz, 1 H, C-6, 7.27 (ddd, J, 0.65, 0.9, 8.2 Hz, 1 H, C-7, 7.70 (ddd, J, 0.65, 1.2, 7.95 Hz, 1 H, C-4, 7.92 (br s, 1 H, N-3′, 8.05 (br s, 1 H, OH, 13C NMR: δ, 16.7 (1′-Me, 32.1 (1-Me, 33.6 (3-CH 2, 37.5 (3′-Me, 108.3 (C-3, 109.4 (C-7, 119.8 (C-4, 120.5 (C-5, 123.6 (C-6, 127.2 (C-3a, 138.0 (C-7a, 138.3 (C-1′, 172.2 (C=O, EIMS: m/z, 255 (71, M, 226 (100, Anal. Calcd for C15H17N3O 255.31, C, 70.56; H, 6.71; N, 16.46. Found: C, 70.76; H, 6.83; N, 16.68
- 3O (255.31): C, 70.56; H, 6.71; N, 16.46. Found: C, 70.76; H, 6.83; N, 16.68.

20
- 48349093737
- The multiplicities and chemical shifts of the aromatic protons have been confirmed after simulation with the program Spin Works, version 2.5, available from
- The multiplicities and chemical shifts of the aromatic protons have been confirmed after simulation with the program Spin Works, version 2.5, available from ftp://davinci.chem.umanitoba.ca.

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