3-Benzyl-2-(furan-2-yl)-1,3-thia­zolidin-4-one

Hoong-Kun Fun; Madhukar Hemamalini; Poovan Shanmugavelan; Alagusundaram Ponnuswamy; Rathinavel Jagatheesan

doi:10.1107/S1600536811039432

. 2011 Sep 30;67(Pt 10):o2807–o2808. doi: 10.1107/S1600536811039432

3-Benzyl-2-(furan-2-yl)-1,3-thiazolidin-4-one

Hoong-Kun Fun ^a,^*,^‡, Madhukar Hemamalini ^a, Poovan Shanmugavelan ^b, Alagusundaram Ponnuswamy ^b, Rathinavel Jagatheesan ^c

PMCID: PMC3201349 PMID: 22064907

Abstract

In the title compound, C₁₄H₁₃NO₂S, the thiazolidine ring is approximately planar with a maximum deviation of 0.112 (1) Å. The furan ring is disordered over two orientations, with an occupancy ratio of 0.901 (5):0.099 (5). The central thiazolidine ring makes dihedral angles of 85.43 (8), 87.50 (11) and 87.9 (9)° with the phenyl ring and the major and minor components of the disordered furan ring, respectively. In the crystal, molecules are connected by weak intermolecular C—H⋯O hydrogen bonds, forming supramolecular chains parallel to the b axis.

Related literature

For details and applications of thiazolidine-4-ones, see: Dutta et al. (1990 ▶); Jadhav & Ingle (1978 ▶); Gursoy et al. (2005 ▶); Rawal et al. (2007 ▶); Shrivastava et al. (2005 ▶); Look et al. (1996 ▶); Anders et al. (2001 ▶); Barreca et al. (2001 ▶); Diurno et al. (1992 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₄H₁₃NO₂S
M _r = 259.31
Monoclinic,
a = 13.2901 (2) Å
b = 9.6360 (1) Å
c = 9.9152 (1) Å
β = 102.855 (1)°
V = 1237.95 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 100 K
0.30 × 0.18 × 0.16 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.928, T _max = 0.961
13239 measured reflections
3551 independent reflections
2794 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.104
S = 1.07
3551 reflections
180 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811039432/rz2640sup1.cif

e-67-o2807-sup1.cif^{(19.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039432/rz2640Isup2.hkl

e-67-o2807-Isup2.hkl^{(170.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811039432/rz2640Isup3.cml

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
C2—H2A⋯O2ⁱ	0.93	2.48	3.355 (3)	158

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Symmetry code: (i) Inline graphic .

Acknowledgments

HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

supplementary crystallographic information

Comment

One of the main objectives of organic and medicinal chemistry is the design, synthesis and production of molecules having value as human therapeutic agents. During the past decade, combinatorial chemistry has provided access to chemical libraries based on privileged structures with heterocyclic moiety receiving special attention as they belong to a class of compounds with proven utility in medicinal chemistry. There are numerous biologically active molecules with five membered rings containing two hetero atoms. Among them, thiazolidin-4-ones are the most extensively investigated class of compounds, which have many interesting activity profiles namely bactericidal (Dutta et al., 1990), antifungal (Jadhav & Ingle, 1978), anticonvulsant (Gursoy et al., 2005), anti-HIV (Rawal et al., 2007), antituberculotic (Shrivastava et al., 2005), COX-1 inhibitors (Look et al., 1996), inhibitors of the bacterial enzyme MurB (Anders et al., 2001), non-nucleoside inhibitors of HIV-RT (Barreca et al., 2001) and anti-histaminic agents (Diurno et al., 1992).

The molecular structure of the title compound is shown in Fig. 1. The thiazolidine (S1/N1/C5–C7) ring is approximately planar, with a maximum deviation of 0.112 (1) Å for atom S1. The furan ring is disordered over two orientations, with an occupancy ratio of 0.901 (5):0.099 (5). The central thiazolidine ring makes dihedral angles of 85.43 (8)°, 87.50 (11) and 87.9 (9)° with the terminal phenyl (C9–C14) ring and the major (O1/C1–C4) and minor (O1X/C1X–C3X/C4) components of the disordered furan ring, respectively. In the crystal structure (Fig. 2), the molecules are connected by weak intermolecular C—H···O (Table 1) hydrogen bonds forming supramolecular chains parallel to the b-axis.

Experimental

To a well ground intimate mixture of triphenylphosphine (1.1 mmol) and furfuraldehyde, (1.0 mmol) in a microwave vial (10 ml) equipped with a magnetic stirring bar, benzylazide (0.2 g, 1.0 mmol) was added dropwise with stirring. Stirring was continued until liberation of nitrogen ceased and then mercaptoacetic acid, (1.1 mmol), was added to the above mixture and the reaction vessel was sealed with a septum. It was then placed into the cavity of a focused monomode microwave reactor (CEM Discover, benchmate) and operated at 150°C (temperature monitored by a built-in IR sensor), power 80W for 10 minutes. The reaction temperature was maintained by modulating the power level of the reactor. The reaction mixture was allowed to stand at room temperature. The residue was then purified by column chromatography on silica (petrolium/ether-ethylacetate, 94:6 v/v) to afford 3-benzyl-2-(furan-2-yl)thiazolidin-4-one. Yield: 0.36 g (94%); M.p: 150–151°C. Crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution.