Cyclo­hexa­nespiro-2′-[2′,3′,6′,7′-tetra­hydro-1′H-cyclo­penta­[d]pyrimidin]-4′(5′H)-one

Daxin Shi; Dongfeng Qian; Qi Zhang; Jiarong Li

doi:10.1107/S1600536809005388

. 2009 Feb 28;65(Pt 3):o615. doi: 10.1107/S1600536809005388

Cyclohexanespiro-2′-[2′,3′,6′,7′-tetrahydro-1′H-cyclopenta[d]pyrimidin]-4′(5′H)-one

Daxin Shi ^a, Dongfeng Qian ^a, Qi Zhang ^a, Jiarong Li ^a,^*

PMCID: PMC2968495 PMID: 21582267

Abstract

The title compound, C₁₂H₁₈N₂O, was synthesized by the reaction of cyclohexanone and 2-aminocyclopent-1-enecarbonitrile. In the molecule of the title compound, the six-carbon ring displays a chair conformation, the six-membered 1,3-diaza ring and the cyclopentene ring both assume envelope conformations. Supramolecular aggregation is achieved by N—H⋯O hydrogen bonds.

Related literature

For general background on the biological activity of pyrimidinones, see: Schramm et al. (1984 ▶); Wen et al. (2002 ▶); For related structures, see: Yu et al. (1992 ▶); Zhang, Li, Shi et al. (2008 ▶); Zhang, Li, Yang et al. (2008 ▶).

Experimental

Crystal data

C₁₂H₁₈N₂O
M _r = 206.28
Monoclinic,
a = 10.294 (2) Å
b = 10.461 (2) Å
c = 10.659 (2) Å
β = 112.70 (3)°
V = 1059.0 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 113 K
0.24 × 0.20 × 0.08 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006 ▶) T _min = 0.980, T _max = 0.993
6976 measured reflections
1862 independent reflections
1632 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.103
S = 1.13
1862 reflections
144 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2006 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809005388/pk2145sup1.cif

e-65-0o615-sup1.cif^{(18KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809005388/pk2145Isup2.hkl

e-65-0o615-Isup2.hkl^{(91.7KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.899 (9)	1.993 (9)	2.8832 (14)	169.9 (14)
N2—H2⋯O1ⁱⁱ	0.899 (9)	2.080 (11)	2.9458 (17)	161.3 (15)

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

We thank the Beijing Institute of Technology for financial support.

supplementary crystallographic information

Comment

Pyrimidin-4(5H)-ones are valuable synthetic intermediates, and represent a common structure found in various biologically active compounds Schramm et al., 1984). Functionalization of the pyrimidin-4(5H)-one group offers an attractive method for the generation of derivatives which may constitute interesting medicinal and biological properties. For example, spiro[cyclohexane-1,2'(1'H)-quinazolin]-4'(3'H)-one shows immunosuppressive, antifungal, and antitumor activity (Wen et al., 2002).

Molecules of the title compound (Fig. 1) are linked by N1—H···O1 and N2—H···O1 H-bonds , as shown in Fig. 2 and have a similar conformation as (s)-2-(3-nitrophenyl)-1,2-dihydro-quinazolin-4(3H)-one (Zhang, Li & Shi et al., 2008). The 1,3-diaza ring assumes envelope conformation, similar to that found in 4(3H)-quinazolinone derivatives (Zhang, Li & Yang et al., 2008; Yu et al., 1992). The cyclopentene exists in an envelope formation, and cyclohexane displays a chair conformation.

Experimental

A solution of 2-aminocyclopent-1-enecarbonitrile (10 mmol, 1.08 g) and sodium methanolate (10 mmol, 0.54 g) in cyclohexanone (2 ml), was refluxed for 2 h. The reaction mixture was cooled to 293 K and kept at this temperature for an additional 12 h. The solvent was filtered in vacuo to give 2-cyclohexyl-2,3,6,7-tetrahydro-1H-cyclopenta[d]pyrimidin- 4(5H)-one. The product was recrystallizated from ethanol to give clearless crytals. M.p. 513–514 K; IR (KBr): 3201 (N—H), 3074, 2931 (C—H), 1707 (C=O) cm^-1; ¹H-NMR(DMSO, p.p.m.): 1.50 (6H, m), 1.74–1.81 (4H, m), 2.28 (2H, t), 2.38 (2H, t), 2.50 (2H, m), 6.57 (1H,s), 6.86 (1H, s). 50 mg of the product was dissolved in ethyl acetate (5 ml) and the solution was kept at room temperature for 4 days to give colorless single crystals.