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6-Amino-2-phenylimidazo[4,5-e][1,3]diazepine-4,8(1H, 5H)-dione

Huan-Ming Chen
Ramachandra S. Hosmane
Laboratory for Drug Design and Synthesis, Department of Chemistry & Biochemistry, University of Maryland, Baltimore County, 1000 Hilltop Circle, Baltimore, MD 21250, USA
Author to whom correspondence should be addressed.
Molecules 2000, 5(7), M164;
Submission received: 17 May 2000 / Accepted: 2 June 2000 / Published: 10 July 2000
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Molecules 05 m164 i001
The starting imidazole diester (1) was prepared by esterification of the corresponding dicarboxylic acid acccording to the literature procedure [1,2]. A solution of dimethyl 2-phenyl-1H-imidazole-4,5-dicarboxylate (1) (0.26 g, 1 mmol) and guanidine hydrochloride (0.48 g, 5 mmol) in 50 mL of absolute methanol was stirred for 30 min at room temperature, then 2 mL of 25% sodium methoxide solution in methanol was added. The resulting mixture was stirred for 48 h at room temperature. The precipitate formed was filtered and washed with methanol to give sodium salt of the product as a white solid. The sodium salt was dissolved in water and neutralized with 2 M hydrochloric acid to yield the title compound (2) as a white solid after filtration and washing with water, yield 0.21 g (78%).
M.p. >260 °C.
TLC (CHCl3: MeOH: 30% NH4OH, 2:2:1): Rf 0.61.
1H NMR (DMSO-d6): 13.74 (br s, 1H, NH, exchangeable with D2O), 10.68 (br s, 1H, NH, exchangeable with D2O), 8.20 (m, 2H, Ph), 7.60 (br s, 1H, NH, exchangeable with D2O), 7.48 (m, 3H, Ph), 6.50 (br s, 1H, NH, exchangeable with D2O).
FABMS: 256 [MH+].
Anal. Calcd. for C12H9N5O2·3/4H2O (268.75): C, 53.63; H, 3.94; N, 26.06. Found: C, 53.62, H, 4.02; N, 26.03.


  1. Anderson, W.K.; Bhattacharjee, D.; Houston, D.M. J. Med. Chem. 1989, 32, 119–127. [CrossRef] [PubMed]
  2. Manecke, G.; Schlegel, R. Chem. Ber. 1974, 107, 892–897. [CrossRef]
Sample availability: available from the authors and from MDPI (MDPI ID 18548).

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MDPI and ACS Style

Chen, H.-M.; Hosmane, R.S. 6-Amino-2-phenylimidazo[4,5-e][1,3]diazepine-4,8(1H, 5H)-dione. Molecules 2000, 5, M164.

AMA Style

Chen H-M, Hosmane RS. 6-Amino-2-phenylimidazo[4,5-e][1,3]diazepine-4,8(1H, 5H)-dione. Molecules. 2000; 5(7):M164.

Chicago/Turabian Style

Chen, Huan-Ming, and Ramachandra S. Hosmane. 2000. "6-Amino-2-phenylimidazo[4,5-e][1,3]diazepine-4,8(1H, 5H)-dione" Molecules 5, no. 7: M164.

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