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Short Note

2-Amino-4,10-dimethylpyrrolo[3,4-b]carbazole-1,3(2H,5H)-dione

by
Norbert Haider
* and
Richard Wanko
Institute of Pharmaceutical Chemistry, University of Vienna, Althanstraße 14, A-1090 Vienna, Austria
*
Author to whom correspondence should be addressed.
Molecules 1999, 4(10), M105; https://doi.org/10.3390/M105
Submission received: 28 August 1998 / Accepted: 1 September 1999 / Published: 8 October 1999
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Versions Notes
Molecules 04 m105 i001
The general part of the experimental section [1] was presented elsewhere. In contrast to analogous cyclization reactions of 1-methyl-2,3-carbazoledicarboxylates which were reported to yield carbazole-fused pyridazinediones [1,2], condensation of dimethyl 1,4-dimethyl-2,3-carbazoledicarboxylate with hydrazine affords a five-membered cyclization product with an N-aminoimide structure. A mixture of dimethyl 1,4-dimethyl-2,3-carbazoledicarboxylate [3] (311 mg, 1 mmol) and 100% hydrazine hydrate (10 ml) was heated at reflux for 1.5 hr. After cooling, the solution was concentrated under reduced pressure to about half of its volume. The precipitate was collected by filtration and it was washed several times with warm ethanol to afford the title compound as fine, pale yellow needles (217 mg, 78%).
M.p. > 330 °C (ethanol)
1H NMR (300 MHz, DMSO-d6): 11.97 (s, 1H, NH), 8.24 (d, J8-9 = 8.1 Hz, 1H, H-9, shows NOE on irradiation at 3.13 ppm), 7.64 (d, J6-7 = 8.1 Hz, 1H, H-6), 7.54-7.47 (m, 1H, H-7), 7.32-7.25 (m, 1H, H-8), 4.78 (s, 2H, NNH2), 3.13 (s, 3H, CH3-10), 2.85 (s, 3H, CH3-4).
IR (cm-1, KBr): 3345 (N-H), 2949, 2920, 1757 (C=O), 1700 (C=O), 1623, 1608, 1521, 1408, 1365, 1330, 1233, 1125, 747, 720, 675, 626 cm-1.
EI-MS: 280 (18%), 279 (100, M+), 263 (37), 234 (29), 218 (18), 206 (42), 205 (40), 193 (34), 192 (41), 191 (44), 190 (22), 165 (20), 140 (27), 96 (18), 83 (38), 63 (15)
Anal. calc. for C16H13N3O2 (279.3): C 68.81, H 4.69, N 15.04; found: C 68.60, H 4.78, N 15.06.

References

  1. Haider, N.; Jbara, R.; Khadami, F.; Wanko, R. Heterocycles 1998, 48, 1609. [CrossRef]
  2. Landelle, H.; LaDuree, D.; Cugnon de Sevricourt, M.; Robba, M. Chem. Pharm. Bull. 1989, 37, 2679. [CrossRef] [PubMed]
  3. Moody, C. J. J. Chem. Soc., Perkin Trans. 1 1985, 2505. [CrossRef]
Sample availability: available from the authors and from MDPI. MDPI ID 17923.

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MDPI and ACS Style

Haider, N.; Wanko, R. 2-Amino-4,10-dimethylpyrrolo[3,4-b]carbazole-1,3(2H,5H)-dione. Molecules 1999, 4, M105. https://doi.org/10.3390/M105

AMA Style

Haider N, Wanko R. 2-Amino-4,10-dimethylpyrrolo[3,4-b]carbazole-1,3(2H,5H)-dione. Molecules. 1999; 4(10):M105. https://doi.org/10.3390/M105

Chicago/Turabian Style

Haider, Norbert, and Richard Wanko. 1999. "2-Amino-4,10-dimethylpyrrolo[3,4-b]carbazole-1,3(2H,5H)-dione" Molecules 4, no. 10: M105. https://doi.org/10.3390/M105

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