Journal of Guangxi Normal University(Natural Science Edition) ›› 2015, Vol. 33 ›› Issue (2): 82-87.doi: 10.16088/j.issn.1001-6600.2015.02.013

Previous Articles     Next Articles

Synthesis and Crystal Structure of Ethyl 5-acetamido-4-(4-chlorophenyl)-2-methyl-6-oxo-5, 6-dihydro-4H-pyran-3-carboxylate

LIANG Xiao-long1,2, HUANG Wan-yun3, PAN Cheng-xue1,2, SU Gui-fa1,2   

  1. 1. State Key Laboratory Cultivation Base for the Chemistry and Molecular Engineering of Medicinal Resources,Guangxi Normal University, Guilin Guangxi 541004, China;
    2. School of Chemistry and Pharmaceutical Sciences,Guangxi Normal University,Guilin Guangxi 541004, China;
    3. Department of Pharmaceutical Sciences, Guilin Medical University, Guilin Guangxi 541004, China
  • Received:2015-01-05 Online:2015-02-10 Published:2018-09-20

PDF (PC)

158

Abstract: Ethyl 5-acetamido-4-(4-chlorophenyl)-2-methyl-6-oxo-5,6-dihydro-4H-pyran-3-carboxylate, C17H18ClNO5, has been synthesized and characterized by IR, NMR, MS and single-crystal X-ray diffraction. The crystal is of orthorhombic, space group Pbca with a=1.189 29(13) nm, b=0.968 44(10) nm, c=3.172 1(2) nm, V=3.653 5(6) nm3, Z=8, Mr=351.77, Dc=1.279 Mg/m3, λ=0.071 073 nm, μ(MoKα)=0.234 mm-1, F (000)=1 472, the final R=0.098 5 and wR=0.245 4 for 141 3 observed reflections with I>2σ(I). The N—H and oxygen atom are involved in intermolecular hydrogen bonds which link the molecules into an one-dimensional chain and stabilize the structure.

Key words: 2-pyrone, synthesis, crystal structure

CLC Number: 

  • O622.5
[1] APPENDINO G, OTTINO M, MARQUEZ N, et al. An anti-inflammatory and anti-HIV-1 phloroglucinol-pyrone from Helichrysum italicum ssp. microphyllum[J]. J Nat Prod, 2007, 70:608-612.
[2] DUARTE F S, DUZZIONI M, MENDES B G, et al. Participation of dihydrostyryl-2-pyrones and styryl-2-pyrones in the central effects of Polygala sabulosa (Polygalaceae), a folk medicine topical anesthetic[J]. Pharmacology, Biochemistry and Behavior, 2007, 86:150-161.
[3] RUBAL J J, MORENO-DORADO F J, GUERRA F M, et al. A pyran-2-one and four meroterpenoids from Thapsia transtagana and their implication in the biosynthesis of transtaganolides[J]. Phytochemistry, 2007, 68:2480-2486.
[4] DIXIT M, RAGHUNANDAN R, KUMAR B, et al. One-pot regioselective synthesis of dihydronaphthofurans and dibenzofurans[J]. Tetrahedron, 2007, 63:1610-1616.
[5] BERTACCHE V, CONTINI A, ERBA E, et al. Synthesis of 4-dialkylaminopyridine derivatives through ring-rearrangement of 3-nitro-2H-pyran-2-one acetamidines[J]. Tetrahedron, 2007, 63:9652-9662.
[6] KUMAR A, SINGH F V, GOEL A. Regioselective synthesis of functionally hindered α-methyl-styrenes through ring transformation of 2H-pyran-2-ones with mesityl oxide[J]. Tetrahedron Lett, 2007, 48:8223-8226.
[7] NELSON H M, STOLTZ B M. Progress toward the synthesis of the basiliolides and transtaganolides:An intramolecular pyrone Diels-Alder entry into a novel class of natural products[J]. Org Lett, 2008, 10:25-28.
[8] SINGH F V, KUMAR A, GOEL A. Synthesis of o,m-cymene-cored biaryls through a carbanion-induced ring transformation strategy[J]. Tetrahedron Lett, 2006, 47:7767-7770.
[9] KIM W S, LEE J H, KANG J, et al. Diels-Alder cycloadditions of 3-phenylamino-5-bromo-2-pyrone for the synthesis of constrained α-amino acid derivatives[J]. Tetrahedron Lett, 2004, 45(8):1683-1687.
[10] MARRISON L R, DICKINSON J M, FAIRLAMB I J. Bioactive 4-substituted-6-methyl-2-pyrones with promising cytotoxicity against A2780 and K562 cell lines[J]. Bioorg Med Chem Lett, 2002, 12:3509-3513.
[11] MARRISON L R, DICKINSON J M, AHMED R, et al. An efficient synthesis of 4-alkenyl/alkynyl-6-methyl-2-pyrones via Pd-catalyzed coupling on 4-bromo-6-methyl-2-pyrone[J]. Tetrahedron Lett, 2002, 43:8853-8857.
[12] MARRISON L R, DICKINSON J M, FAIRLAMB I J. Suzuki cross-coupling approaches to the synthesis of bioactive 3-substituted and 5-substituted-4-methoxy-6-methyl-2-pyrones[J]. Bioorg Med Chem Lett, 2003, 13:2667-2671.
[13] VARA PRASAD J V N, PARA K S, LUNNEY E A, et al. Novel series of achiral, low molecular weight, and potent HIV-1 protease inhibitors[J]. J Am Chem Soc, 1994, 116:6989-6990.
[14] LEE Y S, KIM S N, LEE Y S, et al. Synthesis and HIV protease inhibitory activity of new 4-hydroxy-2-pyrone derivatives[J]. Arch Pharm, 2000, 333:319-322.
[15] SINGH F V, CHAURASIA S, JOSHI M D, et al. Synthesis and in vivo antihyperglycemmic activity of nature-mimicking furanyl-2-pyranones in STZ-S model[J]. Bioorg Med Chem Lett, 2007, 17:2425-2429.
[16] KRISHNA P R, SRINIVAS R. Stereoselective synthesis of (6S)-5,6-dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one[J]. Tetrahedron:Asymmetry, 2007, 18:2197-2200.
[17] FUKUYAMA T, HIGASHIBEPPU Y, YAMAURA R, et al. Ru-catalyzed intermolecular [3+2+1] cycloaddition of α,β-unsaturated ketones with silylacetylenes and carbon monoxide leading to α-pyrones[J]. Org Lett, 2007, 9:587-589.
[18] KOMIYAMA T, TAKAGUCHI Y, TSUBOI S. Novel synthesis of 4-arylsulfenyl-3-hydroxy-2-pyrone:One-pot substitution-rearrangement-cyclization reaction of acetonide-protected 4,5-dihydroxy-2-chloroglycidic ester by sodium arylthiolate[J]. Heterocycles, 2005, 66:503-509.
[19] ZHU Xue-feng, SCHAFFNER A P, LI R C, et al. Phosphine-catalyzed synthesis of 6-substituted 2-pyrones:manifestation of E/Z-Isomerism in the Zwitterionic intermediate[J]. Org Lett, 2005, 7(14):2977-2980.
[20] KOMIYAMA T, TAKAGUCHI Y, GUBAIDULLIN A T, et al. Novel synthesis of 4-halo-3-hydroxy-2-pyrone:one pot rearrangement-cyclization reaction by magnesium halide[J]. Tetrahedron, 2005, 61(9):2541-2547.
[21] CHERRY K, PARRAIN J L, THIBONNET J, et al. Synthesis of isocoumarins and α-pyrones via tandem Stille reaction/heterocyclization[J]. J Org Chem, 2005, 70(17):6669-6675.
[22] PAN Cheng-xue, SU Gui-fa, QIN Jiang-ke. Diastereospecific synthesis of trans-2,3-diaryl-1-aminocyclo-propanecarboxylic acids[J]. Org Prep Proced Int, 2005, 37(3):239-246.
[23] SU Gui-fa, MU Hong-tao, ZA Dan-ming, et al. Stereospecific synthesis of trans-2,3-diaryl substituted 1-aminocyclopropanecarboxylic acid derivatives[J]. Synth Commun, 2003, 33(16):2873-2884.
[24] SHELDRICK G M. SHELXS-97, Program for the solution of crystal structures[CP/CD]. Göttingen, Germany:University of Göttingen, 1997.
[25] SHELDRICK G M. SHELXL-97, Program for the refinement of crystal structures[CP/CD]. Göttingen, Germany:University of Göttingen, 1997.
[1] XIE Tingting, XIE Yao, NI Qingling. Synthesis, Characterization and Crystal Structures of Complexes ContainingOrganic Phosphine Gold Acetylene and Triazoles [J]. Journal of Guangxi Normal University(Natural Science Edition), 2020, 38(4): 92-99.
[2] XU Peng, LI Chaofeng, CHANG Xinwei, ZHANG Yanwu. Synthesis of Water-Soluble Ketone-Aldehyde Resins by Catalysis of Solid Base [J]. Journal of Guangxi Normal University(Natural Science Edition), 2020, 38(3): 70-79.
[3] HUANG Xueren, ZHAO Zhiyuan, JIANG Yimin. Synthesis, Crystal Structure and Luminescent Properties ofa New 2D Coordination Polymer of Zn(Ⅱ)-ttp(4′-(4-carboxyphenyl) -2,2′:6′,2″-terpyridine) [J]. Journal of Guangxi Normal University(Natural Science Edition), 2016, 34(2): 98-104.
[4] WANG Yana, LIN Jiahuang, NI Qingling, ZHANG Fang, YU Ronghua, WANG Xiujian. Synthesis and Crystal Structure of 2-[1,3-bis(2-hydroxy benzyl)-5-pyridyl-4-imidazolidinyl] phenol [J]. Journal of Guangxi Normal University(Natural Science Edition), 2016, 34(2): 105-110.
[5] LIU Han-fu, MA Xian-li, CHEN Su-yi , SHEN Xue-song, HUANG Fu-ping. Synthesis and Antibacterial Activity of Ternary Zinc Complex [J]. Journal of Guangxi Normal University(Natural Science Edition), 2015, 33(4): 103-107.
[6] JIANG Li-ping, HUANG Wan-yun, LIU Dong-cheng, LIANG Fu-pei. Synthesis and Crystal Structures of Zn(Ⅱ) and Cu(Ⅱ) Complexes of 2,2′-dihydroxy[1,1′-binaphthalene]-3,3′-dicarbonylbis(salicylaldehydehydrazone) [J]. Journal of Guangxi Normal University(Natural Science Edition), 2015, 33(1): 93-98.
[7] HUO Hong-yue, LI Zhong-qing, QIN Qi-pin, LIU Yan-cheng, CHEN Zhen-feng. Crystal Structure and Antitumor Activity of Zinc(Ⅱ) Complex with Schiff Bases Derived from 2-Hydroxy-3-methoxybenzaldehyde and 2-(3,4-Methylenedioxyphenyl) ethylamine [J]. Journal of Guangxi Normal University(Natural Science Edition), 2014, 32(3): 65-73.
[8] ZHENG Qing-si, LIN Mei-fang, TANG Huang. Synthesis of N-Methyl Moxifloxacin Hydrochloride and Its Application in Production [J]. Journal of Guangxi Normal University(Natural Science Edition), 2014, 32(2): 101-105.
[9] WU Rui, ZHANG Nan-xi, ZHANG Xiao. Synthesis,Structural Characterization and Magnetic Property of Cu[N(CH2OH)2CH2O](SCN) [J]. Journal of Guangxi Normal University(Natural Science Edition), 2013, 31(4): 78-83.
[10] HUA Shi-xian, WANG Ying-chun, LI Ya-jun, WANG Heng-shan. Synthesis and Optical Properties of 12-Aryl Substituted Derivatives of Methyl Dehydroabietate [J]. Journal of Guangxi Normal University(Natural Science Edition), 2013, 31(2): 64-68.
[11] ZENG Jian-qiang, LIANG Guang-ming, HUANG Ying-da, YANG Kun-guo, GUI Liu-cheng, NI Qing-ling. Hydrogen-bonding Directed Three-dimensional Supramolecular Structure in Catena-((μ2-4,4'-bipyridine)-tetraaqua-cobalt(Ⅱ) bis (2-methylbenzimidazolium-1,3-diacetate) dehydrate): Synthesis and Crystal Structural Characterization [J]. Journal of Guangxi Normal University(Natural Science Edition), 2013, 31(2): 69-75.
[12] SHENG Liang-bing, SHEN Yan-ling, XIONG Bo-pi, ZOU Hua-hong, LIANG Fu-pei. Synthesis,Crystal Structure and Magnetic Properties of [Mn3(oba)3(DMF)4] [J]. Journal of Guangxi Normal University(Natural Science Edition), 2013, 31(2): 76-80.
[13] CHEN Si-yuan, YANG Yang, PENG Yan, LIU Yan-cheng. Crystal Structure and Antitumor Activity of a New Schiff Base Palladium Complex [J]. Journal of Guangxi Normal University(Natural Science Edition), 2013, 31(2): 81-86.
[14] ZHANG Zhong, HU Kun, LIN Xin-liang, SUN Ying-ying. Synthesis,Crystal Structure and Spectroscopic Studies of 2-[2-(1H- 1,2,4-Trizole-1-yl)ethyl]-1H-Benzimidazole Hemihydrate [J]. Journal of Guangxi Normal University(Natural Science Edition), 2013, 31(1): 57-61.
[15] LI Hai-ye, JIANG Yi-min, MENG Xiu-jin. Synthesis and Crystal Structure of Phenanthroline-Cysteic Acid Cobalt(Ⅱ) Ternary Complex [J]. Journal of Guangxi Normal University(Natural Science Edition), 2013, 31(1): 72-75.
Viewed
Full text


Abstract

Cited
  Shared   
  Discussed   
No Suggested Reading articles found!
Copyright © Journal of Guangxi Normal University(Natural Science Edition), All Rights Reserved.
Tel: 0773-5857325　E-mail: gxsdzkb@mailbox.gxnu.edu.cn
Powered by Beijing Magtech Co. Ltd