(1S,6S)-Tetrazolo [1,5-g]-7-Aza-trans-himachal-2-ene

M. Dakir, E. Lassaba and A. Benharref

Laboratoire de Chimie des Substances Naturelles et des Hétérocycles, Département de Chimie, Faculté des Sciences-SemLalia, B.P. 2390, 40001 Marrakech, Maroc. E-mail: [email protected]

Received: 18 February 2001 / Accepted: 15 May 2001 / Published: 25 May 2001

To a solution of 1 (2 g, 9.7 mmol) [1] in trifluoroacetic acid (15 mL) was added by portions during 30 min (1 g, 0.016 mole) sodium azoture [2,3] at -10 °C. After stirring for 24 hours, the reaction mixture was neutralised with 10% of sodium bicarbonate, extracted with ether (3´ 20 mL). The combined organic layers were washed with water, dried over magnesium sulphate, and the solvent was evaporated. The product was purified by column chromatography on neutral alumina using hexane/ether (8/2) as eluant to give 2 (1.67 g 70% yield) as a solid [3].

Mp: 149-150 °C.

¹H NMR (400 MHz, CDCl₃) : 0.85 (s,C14-H₃), 1.10 (s,C15-H₃); 1.75 (s, C12-H₃); 4.65 (td, C6-H J₁=3.8 Hz et J₂=1.5 Hz); 5.4 (s,C2-H).

¹³C NMR (100 MHz, CCl₄) : 47.47 (C1), 38.62 (C2), 135.92 (C3), 121.30 (C4), 24.02 (C5), 59.24 (C6), 156.50 (C8), 28.18 (C9), 22.85 (C10), 23.81 (C11), 36.25 (C12), 22.79 (C13), 29.83 (C14), 32.93 (C15).

SM (m/z) : 246 (M⁺).

References

1. Joseph, T. C.; Sukh, D. Tetrahedron 1968, 24, 3853-3859.
2. Kaye, P. T.; Maphahlele, M. J.; Brown, M. E. J. Chem. Soc. Perkin Trans. 1995, 2, 835-838.
3. Lassaba, E.; Benharref, A.; Giorgi, M.; Pierrot, M. Acta Cryst. 1997, C53, 1139.

Sample Availability: Available from the authors and from MDPI.

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