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Elena B. Usova
Ludmila I. Lysenko
Gennady D. Krapivin
Department of organic chemistry, Kuban State Technological University, Moskovskaya, 2, Krasnodar, 350072, Russian Federation
Author to whom correspondence should be addressed.
Molecules 2000, 5(1), M128;
Submission received: 26 November 1999 / Accepted: 15 December 1999 / Published: 24 January 2000
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Molecules 05 m128 i001
It is known that indazoles have varied biological activity [1,2]. 4-Furyl-6-hydroxy-6-methyl-1,2,4,5,6,7hexahydro-3H-indazole-3-one has been obtained for investigation of its biological activity. To a solution of 3-furyl-5-hydroxy-5-methyl-2-ethoxycarbonylcyclohexanone (1.24 g, 5 mmol) in ethanol (10 ml) were added an aqueous solution of hydrazine hydrate (52 %, 0.5 ml, 5 mmol) and acetic acid (0.5 ml), and the mixture heated to reflux until the reaction was complete (~1.5 h, TLC). The reaction mixture was then cooled to 5-10 °C, the crystalline product was collected, washed with cold ethanol and recrystallized from ethanol to yield 0.97 g (83 %) of hexahydroindazole-3-one as a white crystals.
M.p. 268-269 °C (ethanol).
1H-NMR (CF3COOD, 250 MHz): 7.48 (d, J1=2.0 Hz, 1H, H-5 furan), 6.33 (dd, J1=2.0 Hz, J2=3.6 Hz, 1H, H-4 furan), 6.00 (d, J2=3.6 Hz, 1H, H-3 furan), 4.60 (d, J=3.6 Hz, 1H, 4-H), 2.82 (broad s, 2H, 7-H, 7-H), 2.20 (dd, 1H, J1=6 Hz, J2=14 Hz, 5-H), 1.75 (dd, 1H, J2=14 Hz, J3=11 Hz, 5-H), 1.36 (c, 3H, CH3).
IR (cm-1, nujol): 3270, 3150, 1605, 1600.
UV [lmax(nm), log e (dm3mol-1cm-1)] (ethanol): 208(4,24), 253(3.63).
Anal. calc. for C12H14N2O3 (234,25): C 61.52, H 6.02, N 11.96. Found: C 61.24, H 6.29, N 11.68.

Supplementary Materials

References and Notes

  1. Aran, V.J.; Flores, M.; Munoz, P.; Paez, J.A.; Sanchez-Verdu, P.; Stud, M. Liebigs. Ann. 1996, 683.
  2. Morie, T.; Harada, H.; Kato, S. Synth. Commun. 1997, 27, 559.
Sample Availability: Available from the authors.

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MDPI and ACS Style

Usova, E.B.; Lysenko, L.I.; Krapivin, G.D. 4-Furyl-6-hydroxy-6-methyl-1,2,4,5,6,7-hexahydro-3H-indazole-3-one. Molecules 2000, 5, M128.

AMA Style

Usova EB, Lysenko LI, Krapivin GD. 4-Furyl-6-hydroxy-6-methyl-1,2,4,5,6,7-hexahydro-3H-indazole-3-one. Molecules. 2000; 5(1):M128.

Chicago/Turabian Style

Usova, Elena B., Ludmila I. Lysenko, and Gennady D. Krapivin. 2000. "4-Furyl-6-hydroxy-6-methyl-1,2,4,5,6,7-hexahydro-3H-indazole-3-one" Molecules 5, no. 1: M128.

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