Abstract
C7H5NO, monoclinic, P21/n (no. 14), a = 3.7589(5) Å, b = 19.493(2) Å, c = 8.4180(10) Å, V = 601.98(13) Å3, Z = 4, R gt (F) = 0.0502, wR ref (F2) = 0.1274, T = 170 K.
The molecular structure is shown in Figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.
Data collection and handling.
| Crystal: | Colourless block |
| Size: | 0.15 × 0.12 × 0.08 mm |
| Wavelength: | Mo Kα radiation (0.71073 Å) |
| μ: | 0.09 mm−1 |
| Diffractometer, scan mode: | Bruker APEX-II, φ and ω |
| θmax, completeness: | 26.5°, >99% |
| N(hkl)measured, N(hkl)unique, Rint: | 6761, 1253, 0.075 |
| Criterion for Iobs, N(hkl)gt: | Iobs > 2σ(Iobs), 945 |
| N(param)refined: | 82 |
| Programs: | Bruker [1], Olex2 [2], Shelx [3,4] |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).
| Atom | x | y | z | Uiso*/Ueq |
|---|---|---|---|---|
| C1 | 0.3952 (5) | 0.68836 (10) | 0.7127 (2) | 0.0279 (5) |
| H1 | 0.380367 | 0.709650 | 0.812593 | 0.033* |
| C2 | 0.4694 (5) | 0.72158 (10) | 0.5732 (2) | 0.0290 (5) |
| H2 | 0.513857 | 0.769072 | 0.561137 | 0.035* |
| C3 | 0.4638 (6) | 0.67189 (10) | 0.4615 (2) | 0.0299 (5) |
| H3 | 0.504792 | 0.679362 | 0.355424 | 0.036* |
| C4 | 0.3496 (5) | 0.62080 (10) | 0.6770 (2) | 0.0242 (5) |
| C5 | 0.2630 (5) | 0.56344 (10) | 0.7672 (2) | 0.0249 (5) |
| H5 | 0.217764 | 0.572413 | 0.871981 | 0.030* |
| C6 | 0.2400 (5) | 0.49831 (10) | 0.7170 (2) | 0.0267 (5) |
| H6 | 0.288485 | 0.487902 | 0.613531 | 0.032* |
| C7 | 0.1454 (5) | 0.44370 (10) | 0.8131 (2) | 0.0266 (5) |
| N1 | 0.0695 (5) | 0.39881 (9) | 0.8877 (2) | 0.0326 (5) |
| O1 | 0.3916 (4) | 0.60939 (7) | 0.52050 (15) | 0.0281 (4) |
Source of material
The substrate 2-furanacrylamide (1.0 mmol), (EtO)3SiH (3.0 mmol), phenylselenophenol iron complex (2 mol%) as catalyst and tetrahydrofuran (THF) (2 mL) were added into a 25 mL Schlenk tube in a nitrogen atmosphere at room temperature. The reaction mixture was stirred at 60 °C for 24 h. The reaction progress was detected by gas chromatography (GC) and thin layer chromatography (TLC). After the reaction, the product was extracted using petroleum ether (10 ml) three times, and the organic phase were combined together and dried with anhydrous Na2SO4. The organic solvents were removed by vacuum distillation. Crude products were purified by gel column chromatography and finally recrystallized to obtain the title compound.
Experimental details
All hydrogen atoms were placed in calculated positions and refined as riding atoms. The Uiso values were constrained to be 1.2Ueq. All the H atoms were refined as riding on their parent atom.
Comment
Furan derivatives have a unique status and important feature in a variety of natural products [5, 6]. They are widely used in some important commercial products, like dyes, essential oils, cosmetic, industrial preservative, bioregulators, photosensitizers, fire retardants, and flavoring compounds [7], [8], [9], [10]. Additionally, furan analogues show abundant pharmacological properties, like anti-depressant, anti-inflammatory, anti-hypertensive, anti-ageing, anti-cancer, anti-ulcer, anti-oxidation, and anti-glaucoma effects [11], [12], [13], [14], [15], [16], which engage the attention of medicinal chemists to synthesize a series of furan-based derivatives [5]. For example, furan-2-carboxamide and 2-furyl acetonitrile derivatives [6, 17] have found use as key intermediates to synthesize new candidates for anti-cancer drugs.
The asymmetric unit of the title structure contains one molecule (see the Figure). Weak intermolecular C–H⋯O and C–H⋯N hydrogen bonds are observed. Additionally, a weak intramolecular hydrogen C6–H6⋯O1 bond interaction is also formed between O1 and H6 atoms. The C7–N1 distance is 1.149(3) Å, which indicates a C–N triple bond. The three N1–C7–C6 atoms with the bond angle of 178.5(3)° are almost in a straight line. Weak hydrogen bond interactions connect the molecular structures into a three-dimensional network. For example, there is a weak C–H⋯O interaction (2.6282(15) Å) between H6 atom and the O1 atom of the adjacent molecule. The similar intermolecular interaction (C–H⋯N, 2.5958(18) Å) was observed in the H2 and N1 atoms. All geometric parameters are as expected [18].
Acknowledgements
We gratefully acknowledge support by the key scientific research projects of colleges and universities in Henan Province for financial support (22A430032).
-
Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
-
Research funding: Key Scientific Research Projects of Colleges and Universities in Henan Province for financial support (22A430032).
-
Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
References
1. Bruker. SMART APEX-II CCD; Bruker AXS Inc.: Madison, WI, USA, 2006.Search in Google Scholar
2. Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K., Puschmann, H. OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Crystallogr. 2009, 42, 339–341; https://doi.org/10.1107/s0021889808042726.Search in Google Scholar
3. Sheldrick, G. M. Crystal structure refinement with SHELXL. Acta Crystallogr. 2015, C71, 3–8; https://doi.org/10.1107/s2053229614024218.Search in Google Scholar
4. Sheldrick, G. M. SHELXTL – integrated space-group and crystal-structure determination. Acta Crystallogr. 2015, A71, 3–8; https://doi.org/10.1107/s2053273314026370.Search in Google Scholar
5. Banerjee, R., Hks, K., Banerjee, M. Medicinal significance of furan derivatives: a review. Int. J. Res. Phytochem. Pharm. 2015, 5, 48–57.Search in Google Scholar
6. Mouradzadegun, A., Abadast, F. Thermally-induced ring contraction as a novel and straightforward route for the synthesis of 2-furyl acetonitrile derivatives. Tetrahedron Lett. 2013, 54, 2641–2644; https://doi.org/10.1016/j.tetlet.2013.03.033.Search in Google Scholar
7. Sayahi, M. H., Adib, M., Hamooleh, Z., Zhu, L., Amanlou, M. Reaction between furan- or thiophene-2-carbonyl chloride, isocyanides, and dialkyl acetylenedicarboxy-lates: multicomponent synthesis of 2,2′-bifurans and 2-(thiophen-2-yl)furans. Helv. Chim. Acta 2015, 98, 1231–1239; https://doi.org/10.1002/hlca.201500005.Search in Google Scholar
8. Rahmati, A., Pashmforoush, N. Synthesis of various heterocyclic compounds via multi-component reactions in water. J. Iran. Chem. Soc. 2015, 12, 993–1036; https://doi.org/10.1007/s13738-014-0562-z.Search in Google Scholar
9. Al-Fakih, A. M., Aziz, M., Abdallah, H. H., Algamal, Z. Y., Lee, M. H., Maarof, H. High dimensional QSAR study of mild steel corrosion inhibition in acidic medium by furan derivatives. Int. J. Electrochem. Sci. 2015, 10, 3568–3583.Search in Google Scholar
10. Santonicola, S., Mercogliano, R. Occurrence and production of furan in commercial foods. Ital. J. Food Sci. 2016, 28, 155.Search in Google Scholar
11. de Paulis, T Drug evaluation: vilazodone-a combined SSRI and 5-HT1A partial agonist for the treatment of depression. IDrugs 2007, 10, 193–201.Search in Google Scholar
12. Viola, G., Vedaldi, D., dall’Acqua, F., Basso, G., Disarò, S., Spinelli, M., Cosimelli, B., Boccalini, M., Chimichi, S. Synthesis, cytotoxicity, and apoptosis induction in human tumor cells by geiparvarin analogues. Chem. Diodivers. 2004, 1, 1265–1280; https://doi.org/10.1002/cbdv.200490089.Search in Google Scholar
13. Hodgson, R. A., Bertorelli, R., Varty, G. B., Lachowicz, J. E., Forlani, A., Fredduzzi, S., Cohen–Williams, M. E., Higgins, G. A., Impagnatiello, F., Nicolussi, E. Characterization of the potent and highly selective A2A receptor antagonists preladenant and SCH 412348 [7-[2-[4-2,4-difluorophenyl]- 1-piperazinyl]ethyl]-2-(2-furanyl)-7H-pyrazolo[4,3-e][1,2,4] triazolo[1,5-c]pyrimidin-5-amine] in rodent models of movement disorders and depression. J. Pharmacol. Exp. Therapeut. 2009, 330, 294–303; https://doi.org/10.1124/jpet.108.149617.Search in Google Scholar
14. Shwetha, B., Sudhanva, M. S., Jagadeesha, G. S., Thimmegowda, N. R., Hamse, V. K., Sridhar, B. T., Thimmaiah, K. N., Ananda Kumar, C. S., Shobith, R., Rangappa, K. S. Furan-2-carboxamide derivative, a novel microtubule stabilizing agent induces mitotic arrest and potentiates apoptosis in cancer cells. Bioorg. Chem. 2021, 108, 104586; https://doi.org/10.1016/j.bioorg.2020.104586.Search in Google Scholar
15. Kumar, N., Gusain, A., Kumar, J., Singh, R., Hota, P. K. Anti-oxidation properties of 2-substituted furan derivatives: a mechanistic study. J. Lumin. 2021, 230, 117725; https://doi.org/10.1016/j.jlumin.2020.117725.Search in Google Scholar
16. Alizadeh, M., Jalal, M., Hamed, K., Saber, A., Kheirouri, S., Pourteymour, F., Kamari, N. Recent updates on anti-inflammatory and antimicrobial effects of furan natural derivatives. J. Inflamm. Res. 2020, 13, 451–463; https://doi.org/10.2147/jir.s262132.Search in Google Scholar
17. Shwetha, B., Sudhanva, M. S., Jagadeesha, G. S., Thimmegowda, N. R., Hamse, V. K., Sridhar, B. T., Thimmaiah, K. N., Ananda Kumar, C. S., Shobith, R., Rangappa, K. S. Furan-2-carboxamide derivative, a novel microtubule stabilizing agent induces mitotic arrest and potentiates apoptosis in cancer cells. Bioorg. Chem. 2021, 108, 104586; https://doi.org/10.1016/j.bioorg.2020.104586.Search in Google Scholar
18. Pomes Hernandez, R., Duque Rodriguez, J., Villena Rodriguez, R., Soriano Garcia, M. Two cyanacrylamides. Acta Crystallogr. 1995, C51, 1575–1577; https://doi.org/10.1107/s0108270194000442.Search in Google Scholar
© 2022 Lilei Zhang and Tianyu Mi, published by De Gruyter, Berlin/Boston
This work is licensed under the Creative Commons Attribution 4.0 International License.
