Synthesis of 4-Amino-1,7,8,9-tetramethyl-4-aza-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

Struga, Marta; Kossakowski, Jerzy

doi:10.3390/M534

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Synthesis of 4-Amino-1,7,8,9-tetramethyl-4-aza-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

by

Marta Struga

^* and

Jerzy Kossakowski

The Medical University, Department of Medical Chemistry, 3 Oczki Str., 02-007 Warsaw, Poland

^*

Author to whom correspondence should be addressed.

Molbank 2007, 2007(2), M534; https://doi.org/10.3390/M534

Submission received: 27 September 2006 / Accepted: 16 January 2007 / Published: 31 May 2007

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Keywords:

1,7,8,9-Tetramethyl-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione; 4-Amino-1,7,8,9-tetramethyl-4-aza-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione; hydrazine hydrate

Various imide derivatives of 1,7,8,9-tetramethyl-4-aza-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione (2) have been reported and shown to exhibit an anxiolytic activities [1].

Starting materials e.g. 1,2,3,4-tetramethyl-1,3-cyclopentadiene, and furan-2,5-dione were commercially available reagents.

1,7,8,9-Tetramethyl-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione (1).

The synthesis of (1) was performed from 1,2,3,4-tetramethyl-1,3-cyclopentadiene and furan-2,5-dione according to the method described previously [2]. (Lit. m.p. 108-109⁰C. Yield 68 %.)

White crystals, yield 76 %.

Melting point: 110°C.

¹H NMR (400 MHz, CDCl₃) δ (ppm): 3.35 (s, 2H, CH-C=O); 3.29 (s, 12H, CH₃); 2.72 (s, 2H, CH₂).

¹³C-NMR (100 MHz, CDCl₃) δ (ppm): 171.3, 138.4, 137.6, 63.9, 56.3, 54.4, 16.6, 11.0.

ESI MS: m/z = 243.3 [M + Na]⁺ (100%).

Elemental Analysis: Calculated for C13H16O3 (220.26): C, 70.89 %; H, 7.32 %. Found: C, 70.92 %; H, 7.23 %.

4-Amino-1,7,8,9-tetramethyl-4-aza-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione (2).

A mixture of anhydride 1 (0.01 mole) and hydrazine hydrate (80% water solution) (10 ml) was refluxed for 5 h. The solvents were evaporated. The residue was purified by a column chromatography (silica gel, chloroform/methanol 19:1) to give compound 2.

White crystals, yield 89 %.

Melting point: 161°C.

¹H NMR (400 MHz, CDCl₃) δ (ppm): 4.52 (s, 2H, NH₂); 3.02 (s, 2H, CH-C=O); 1.53 (s, 6H, CH₃); 1.47 (s, 6H, CH₃); 1.33 (dd, 2H, CH₂).

¹³C-NMR (100 MHz, CDCl₃) δ (ppm): 174.4, 137.6, 63.6, 55.2, 51.9, 17.1, 10.9.

ESI MS: m/z = 257.2 [M + Na]⁺ (100%).

Elemental Analysis: Calculated for C13H18O2N2(234.3): C, 66.07 %; H, 8.53 %; N, 11.85 %. Found: C, 66.32 %; H, 8.32 %; N, 11.89 %.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3Supplementary File 4Supplementary File 5Supplementary File 6

References

Kossakowski, J.; Kuśmierczyk, J. Acta Pol. Pharm. 1999, 56, 94.
Mironov, V.A.; Sobolev, E.V.; Elizarova, A.N. Tetrahedron 1963, 19, 1939.

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Struga, M.; Kossakowski, J. Synthesis of 4-Amino-1,7,8,9-tetramethyl-4-aza-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione. Molbank 2007, 2007, M534. https://doi.org/10.3390/M534

AMA Style

Struga M, Kossakowski J. Synthesis of 4-Amino-1,7,8,9-tetramethyl-4-aza-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione. Molbank. 2007; 2007(2):M534. https://doi.org/10.3390/M534

Chicago/Turabian Style

Struga, Marta, and Jerzy Kossakowski. 2007. "Synthesis of 4-Amino-1,7,8,9-tetramethyl-4-aza-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione" Molbank 2007, no. 2: M534. https://doi.org/10.3390/M534

APA Style

Struga, M., & Kossakowski, J. (2007). Synthesis of 4-Amino-1,7,8,9-tetramethyl-4-aza-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione. Molbank, 2007(2), M534. https://doi.org/10.3390/M534

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Synthesis of 4-Amino-1,7,8,9-tetramethyl-4-aza-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

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