Synthesis of N-acetyl-N-(3,5-dioxo-10-oxa-4-aza-tricyclo[5.2.1.02,6]dec-4-yl)-acetamide

Struga, Marta; Kossakowki, Jerzy; Mirosław, Barbara; Kozioł, Anna E.

doi:10.3390/M533

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Synthesis of N-acetyl-N-(3,5-dioxo-10-oxa-4-aza-tricyclo[5.2.1.0^2,6]dec-4-yl)-acetamide

by

Marta Struga

^1,*,

Jerzy Kossakowki

¹,

Barbara Mirosław

¹ and

Anna E. Kozioł

¹

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

²

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), M533; https://doi.org/10.3390/M533

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

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Keywords:

4-amino-10-oxa-4-aza-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione; acylation

Various imide derivatives of 10-Oxa-4-aza-tricyclo[5.2.1.0^2,6]decane-3,5-dione have been reported and shown to exhibit a wide spectrum of biological activities including antitumor properties [1].

4-Amino-10-oxa-4-aza-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione (1) was used as a starting material. This compound was obtained in Diels-Alder reaction of furan and furan-2,5-dione [2] and next treated with hydrazine (80% aqueous solution) [3]. Compound 2 was obtained in acylation reaction of compound 1. The reduction of compound 2 occurred during the acylation.

N-acetyl-N-(3,5-dioxo-10-oxa-4-aza-tricyclo[5.2.1.0^2,6]dec-4-yl)-acetamide (2).

0.01 Mole of the compound 1and 10 ml of acetic anhydride were heated while boiling for 6h under reflux condenser. The reaction mixture was filtered off and the solvent was removed under a reduced pressure. The residue was crystallized from ethanol. Next it was purified by column chromatography (silica gel) using chloroform/methanol (19:1) as eluent.

White crystals, yield 78 %.

Melting point: 128 °C.

¹H NMR (400 MHz, CDCl₃) δ (ppm): 4.96 (s, 2H, CH-O); 3.1 (s, 2H, CH-C=O); 2.59 (s, 3H, CH₃); 2.11 (s, 3H, CH₃); 1.93 (m, 2H, CH₂); 1.68 (m, 2H, CH₂).

¹³C-NMR (100 MHz, CDCl₃) δ (ppm): 174.3, 136.1, 79.8, 45.0, 38.8.

ESI MS: m/z = 289.2 [M + Na]⁺ (100%).

Elemental Analysis: Calculated for C12H14N2O5 (266.25) calculated: C, 54.13 %; H, 5.30%; N, 10.52 %. Found: C, 54.18 %; H, 45.32 %; N, 10.72 %.

Crystal data for (2): C₁₂H₁₄N₂O₅, M.W. = 266.25, crystal system orthorhombic, space group Pbca with unit cell dimensions a = 6.977(1), b = 16.658(3), c = 21.361(4) A and V = 2482.6(7) A^-3; Z = 8, d(calc) = 1.425 g cm^-3, m= 0.952 mm^-1, F(000) = 1120.

Cis, exo configuration at the ring junction; the N,N-diacetyl fragment is planar with perpendicular orientation to the imid ring plane; the C=O bonds of acetyl groups are anti.

The diffraction data were collected at 275 K on a KM-4 diffractomater using the crystal of dimensions 0.22 ‘ 0.15 ’ 0.11 mm and CuKa radiation. Within the q range of 5.3 to 72.2°, 2445 reflections were collected. The structure was solved by direct methods and refined by full-matrix least-squares on F² (programs SHELXS97 and SHELXL97 [4,5]). The refinement of 175 parameters converged at final R indices:

R₁ = 0.0311, wR₂ = 0.0889 (for 1039 observed reflections, I > 2s (I)) and R₁ = 0.1377, wR₂ = 0.1188 (all data), and Goof = 0.996. The extinction coefficient was 0.0032(3), residual electron density Dr (max) = 0.20 and Dr (min) = -0.18 e A^-3.

Figure 1. Perspective view of molecular structure of compound 2

Table 1. Bond lengths (Å)

**Table 1.** Bond lengths (Å)
N(1)-N(2)	1.383(2)	C(3)-C(4)	1.525(3)
N(1)-C(1)	1.393(3)	C(3)-C(8)	1.542(3)
N(1)-C(2)	1.396(3)	C(4)-C(5)	1.529(3)
N(2)-C(10)	1.416(2)	C(5)-C(6)	1.537(3)
N(2)-C(11)	1.420(3)	C(6)-C(7)	1.521(3)
O(1)-C(1)	1.205(3)	C(7)-C(8)	1.542(3)
O(2)-C(2)	1.201(2)	C(10)-C(12)	1.490(3)
O(3)-C(4)	1.440(2)	C(11)-C(13)	1.486(3)
O(3)-C(7)	1.442(3)	N(2)-N(1)-C(1)	122.5(2)
O(4)-C(10)	1.198(2)	N(2)-N(1)-C(2)	123.2(2)
O(5)-C(11)	1.199(2)	C(1)-N(1)-C(2)	114.0(2)
C(1)-C(8)	1.489(3)	C(1)-N(1)-N(2)-C(10)	93.2(2)
C(2)-C(3)	1.508(2)	C(2)-N(1)-N(2)-C(11)	90.6(2)

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

References

Walter, W.G. J. Pharm. Sci. 1989, 78, 66. [PubMed]
Kwart, H.; Burchuk, J. J. Am. Chem. Soc. 1952, 74, 3094.
Struga, M.; Mirosław, B.; Wawrzyca-Gorczyca, I.; Kossakowski, J.; Kozioł, A.E. Polish J. Chem. 2007, 81, 51.
Sheldrick, G.M. SHELXS-93: Program for crystal structure solution. University of Göttingen: Germany, 1993. [Google Scholar]
Sheldrick, G.M. SHELXL-97: Program for the refinement of crystal structures from diffraction data. University of Göttingen: Germany, 1997. [Google Scholar]

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Struga, M.; Kossakowki, J.; Mirosław, B.; Kozioł, A.E. Synthesis of N-acetyl-N-(3,5-dioxo-10-oxa-4-aza-tricyclo[5.2.1.0^2,6]dec-4-yl)-acetamide. Molbank 2007, 2007, M533. https://doi.org/10.3390/M533

AMA Style

Struga M, Kossakowki J, Mirosław B, Kozioł AE. Synthesis of N-acetyl-N-(3,5-dioxo-10-oxa-4-aza-tricyclo[5.2.1.0^2,6]dec-4-yl)-acetamide. Molbank. 2007; 2007(2):M533. https://doi.org/10.3390/M533

Chicago/Turabian Style

Struga, Marta, Jerzy Kossakowki, Barbara Mirosław, and Anna E. Kozioł. 2007. "Synthesis of N-acetyl-N-(3,5-dioxo-10-oxa-4-aza-tricyclo[5.2.1.0^2,6]dec-4-yl)-acetamide" Molbank 2007, no. 2: M533. https://doi.org/10.3390/M533

APA Style

Struga, M., Kossakowki, J., Mirosław, B., & Kozioł, A. E. (2007). Synthesis of N-acetyl-N-(3,5-dioxo-10-oxa-4-aza-tricyclo[5.2.1.0^2,6]dec-4-yl)-acetamide. Molbank, 2007(2), M533. https://doi.org/10.3390/M533

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Synthesis of N-acetyl-N-(3,5-dioxo-10-oxa-4-aza-tricyclo[5.2.1.0^2,6]dec-4-yl)-acetamide

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