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Synthesis and Crystal Structure of 2-(1-Naphthalenylamino)-4-thiazolidinone

Synthesis and Crystal Structure of 2-(1-Naphthalenylamino)-4-thiazolidinone
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摘要 The compound 2-(1-naphthalenylamino)-4-thiazolidinone was synthesized by the reaction of 1-(naphthalene-1-yl)thiourea with ethyl chloroacetate in an ionic liquid, and its structure was characterized by IR, 1H NMR and single-crystal X-ray diffraction. The crystal of the title compound belongs to monoclinic, space group P21 /c with a=10.0081(3), b=14.5312(4), c=7.8739(2) , β=99.425(3)°, Z=4, V=1129.64(5)3 , Dc=1.425 g/cm3 , μ=0.269 mm-1 , F(000)=504, the final R=0.0519 and wR=0.1507. X-ray analysis indicated that the five-membered ring is essentially planar in this molecule, and intermolecular hydrogen bonds N(1)-H(1)…N(2), C(3)-H(3)…O(1), C(4)-H(4)…O(1) and C(12)-H(12a)…O(1) were observed. π-π Stacking interactions contribute to the stability of the structure. DSC-TG analysis showed that the title compound experienced a phase change at 190 ℃ and began to decompose above 240 ℃. The compound 2-(1-naphthalenylamino)-4-thiazolidinone was synthesized by the reaction of 1-(naphthalene-1-yl)thiourea with ethyl chloroacetate in an ionic liquid, and its structure was characterized by IR, 1H NMR and single-crystal X-ray diffraction. The crystal of the title compound belongs to monoclinic, space group P21 /c with a=10.0081(3), b=14.5312(4), c=7.8739(2) , β=99.425(3)°, Z=4, V=1129.64(5)3 , Dc=1.425 g/cm3 , μ=0.269 mm-1 , F(000)=504, the final R=0.0519 and wR=0.1507. X-ray analysis indicated that the five-membered ring is essentially planar in this molecule, and intermolecular hydrogen bonds N(1)-H(1)…N(2), C(3)-H(3)…O(1), C(4)-H(4)…O(1) and C(12)-H(12a)…O(1) were observed. π-π Stacking interactions contribute to the stability of the structure. DSC-TG analysis showed that the title compound experienced a phase change at 190 ℃ and began to decompose above 240 ℃.
出处 《Chinese Journal of Structural Chemistry》 SCIE CAS CSCD 2012年第7期977-980,共4页 结构化学(英文)
基金 supported by the Natural Science Foundation of Zhejiang Province (Y4080234)
关键词 crystal structure ionic liquid 4-THIAZOLIDINONE X-ray diffraction thermal analysis crystal structure, ionic liquid, 4-thiazolidinone, X-ray diffraction, thermal analysis
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  • 1Kucukguzel, S. G.; Oruc, E. E.; Rollas, S.; Sahin, F.; Ozbek, A. Synthesis, characterization and biological activity of novel 4-thiazolidinones, 1,3,4-oxadiazoles and some related compounds. Etr. ,I. Med Chem. 2002, 37, 197-206.
  • 2Bonde, C. G.; Gaikwad, N..l. Synthesis and preliminary evaluation of some pyrazine containing thiazolines and thiazolidinoncs as antimicrobial agents. Bioorg. Med Chem. 2004, 12, 2151-2161.
  • 3Unangst, P. C.; Connor, D. T.; Cetenko, W. A.; Sorenson, R. J.; Kostlan, C. R.; Sircar, J. C.; Wright, C. D.; Schrier, D. J.: Dyer, R. D. Synthesis and biological evaluation of 5-[[3,5-bis(1,l-dimethylethyl)-4-hydroxyphenyl]methylene]oxazoles, -thiazoles, and -imidazoles: novel dual 5-1ipoxygenase and cyclooxygenase inhibitors with antiinflammatory activity. J. Med. Chem. 1994, 37,322-32g.
  • 4Parmar, S. S.; Dwivedi, C.; Chaudhari, A.; (3upta, T. K. Substituted thiazolidones and their selective inhibition of nicotinamide-adenine dinucleotide dependent oxidations..I. Med Chem. 1972, 15, 99-101.
  • 5Amin, K. M.; Rahman, D. E. A.; A1-Eryani, Y. A. Synthesis and preliminary evaluation of some substituted coumarins as anticonvulsant agents. Bioorg. Med Chem. 2008, I6, 5377-5388.
  • 6Zhou, H. Y.; Wu, S. H.; Zhai, S. M.; Liu, A. F.; Sun, Y.; Li, R. S.; Zhang, Y.; Ekins, S.; Swaan, P. W.; Fang, B. L.; Zhang, B.; Yan, B. Design, synthesis, cytoseleetive toxicity, structure-activity relationships, and pharmacophore of thiazolidinonc derivatives targeting drug-resistant lung cancer cells. J. Med. Chem. 20.08.51, 1242 1251.
  • 7Shcldrick, G. M. A short history of SHELX. Acta Ctyst. 2008, A64, 112-122.

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