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Short Note

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

by
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
*
Author to whom correspondence should be addressed.
Molecules 2001, 6(6), M227; https://doi.org/10.3390/M227
Submission received: 18 February 2001 / Accepted: 15 May 2001 / Published: 25 May 2001
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Versions Notes
Molecules 06 m227 i001
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+).

Supplementary Materials

References

  1. Joseph, T. C.; Sukh, D. Tetrahedron 1968, 24, 3853–3859. [CrossRef]
  2. Kaye, P. T.; Maphahlele, M. J.; Brown, M. E. J. J. Chem. Soc. Perkin Trans. 1995, 2, 835–838. [CrossRef]
  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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MDPI and ACS Style

Dakir, M.; Lassaba, E.; Benharref, A. (1S,6S)-Tetrazolo [1,5-g]-7-Aza-trans-himachal-2-ene. Molecules 2001, 6, M227. https://doi.org/10.3390/M227

AMA Style

Dakir M, Lassaba E, Benharref A. (1S,6S)-Tetrazolo [1,5-g]-7-Aza-trans-himachal-2-ene. Molecules. 2001; 6(6):M227. https://doi.org/10.3390/M227

Chicago/Turabian Style

Dakir, M., E. Lassaba, and A. Benharref. 2001. "(1S,6S)-Tetrazolo [1,5-g]-7-Aza-trans-himachal-2-ene" Molecules 6, no. 6: M227. https://doi.org/10.3390/M227

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