Crystal Structure of Ethyl 6-Amino-5-cyano-4-(4-fluorophenyl)-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylate

被引：0
|
作者：
Kumar, Balbir [1 ]
Banerjee, Bubun [2 ]
Brahmachari, Goutam [2 ]
Gupta, Vivek K. [1 ]
机构：
[1] Univ Jammu, Postgrad Dept Phys & Elect, Xray Crystallog Lab, Jammu, India
[2] Visva Bharati, Dept Chem, Lab Nat Prod & Organ Synth, Santini Ketan, W Bengal, India
来源：
CRYSTALLOGRAPHY REPORTS | 2018年 / 63卷 / 03期
关键词：
BIOLOGICAL-ACTIVITY;
D O I：
10.1134/S1063774518030057
中图分类号：
O7 [晶体学];
学科分类号：
0702 ; 070205 ; 0703 ; 080501 ;
摘要：
Ethyl 6-amino-5-cyano-4-(4-fluorophenyl)-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylate was synthesized based on a commercially available trisodium citrate dihydrate as an inexpensive and eco-friendly catalyst for the first-time via one-pot tandem Knoevenagel-cyclocondensation of malononitrile, 4-fluorobenzaldehyde and in situ generated ethyl 5-oxo-2,5-dihydro-1H-pyrazole-3-carboxylate in aqueous ethanol at room temperature and its crystal structure is determined by X-ray structure analysis. The crystals are triclinic, sp. gr. P\l=1_\ a = 8.7914(7) &, b = 11.3632(8) &, c = 11.4005(9) &, alpha = 62.278(7)degrees, (beta = 71.099(7)degrees, gamma = 80.856(6)degrees, Z=2,R = 0.0544 for 2491 observed reflections. Pyran and pyrazole rings are almost coplanar and phenyl ring is almost perpendicular to these two rings. Pyran ring adopts boat conformation. The crystal structure is stabilized by NHN, NHO, CHF, and CH-pi hydrogen interactions. In addition, a number of weak pi pi interactions also contribute to stabilize the crystal structure.
引用
收藏
页码：388 / 393
页数：6
相关论文
共 50 条
  • [1] Crystal Structure of Ethyl 6-Amino-5-cyano-4-(4-fluorophenyl)- 2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylate
    Balbir Kumar
    Bubun Banerjee
    Goutam Brahmachari
    Vivek K. Gupta
    Crystallography Reports, 2018, 63 : 388 - 393
  • [2] Ethyl 6-amino-5-cyano-4-phenyl-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylate dimethyl sulfoxide monosolvate
    Sharma, Naresh
    Brahmachari, Goutam
    Banerjee, Bubun
    Kant, Rajni
    Gupta, Vivek K.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2014, 70 : 0795 - +
  • [3] Methyl 6-amino-5-cyano-4-(4-fluorophenyl)-2-methylpyridine-3-carboxylate
    Wang, Qian
    Zhou, Dianxiang
    Li, Chunmei
    Shao, Qingqing
    Tu, Shujiang
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2007, 63 : O4220 - U2489
  • [4] New synthesis of ethyl 6-amino-4-aryl-5-cyano-1,4-dihydropyrano[2,3-c]pyrazole-3-carboxylates
    V. L. Gein
    T. M. Zamaraeva
    I. V. Kozulina
    Russian Journal of Organic Chemistry, 2014, 50 : 691 - 693
  • [5] New synthesis of ethyl 6-amino-4-aryl-5-cyano-1,4-dihydropyrano[2,3-c]pyrazole-3-carboxylates
    Gein, V. L.
    Zamaraeva, T. M.
    Kozulina, I. V.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 50 (05) : 691 - 693
  • [6] A novel four-component, synthesis of ethyl 6-amino-4-aryl-5-cyano-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylates
    Gein, V. L.
    Zamaraeva, T. M.
    Slepukhin, P. A.
    TETRAHEDRON LETTERS, 2014, 55 (33) : 4525 - 4528
  • [7] Synthesis of 6-amino-4-aryl-5-cyano-3-(3-cyanopyridin-2-ylthiomethyl)2,4-dihydropyrano[2,3-c]pyrazoles and their hydrogenated analogs.: Molecular structure of 6-amino-5-cyano-3-(3-cyano-4,6-dimethylpyridin-2-ylthiomethyl)-4-(2-nitrophenyl)-2,4-dihydropyrano[2,3-c]pyrazole
    Rodinovskaya, LA
    Gromova, AV
    Shestopalov, AM
    Nesterov, VN
    RUSSIAN CHEMICAL BULLETIN, 2003, 52 (10) : 2207 - 2213
  • [8] Synthesis of 6-amino-4-aryl-5-cyano-3-(3-cyanopyridin-2-ylthiomethyl)-2,4-dihydropyrano[2,3-c]pyrazoles and their hydrogenated analogs. Molecular structure of 6-amino-5-cyano-3-(3-cyano-4,6-dimethylpyridin-2-ylthiomethyl)-4-(2-nitrophenyl)-2,4-dihydropyrano[2,3-c]pyrazole
    L. A. Rodinovskaya
    A. V. Gromova
    A. M. Shestopalov
    V. N. Nesterov
    Russian Chemical Bulletin, 2003, 52 : 2207 - 2213
  • [9] 6-Amino-3-methyl-4-(3,4,5-trimethoxyphenyl)-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
    Sharma, Naresh
    Brahmachari, Goutam
    Banerjee, Bubun
    Kant, Rajni
    Gupta, Vivek K.
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2014, 70 : O875 - +
  • [10] Crystal Structure and Molecular Conformational Studies of Allyl 6-Amino-5-cyano-4-(4-fluorophenyl)-2-methyl-4H-pyran-3-carboxylate
    T. Mohandas
    C. Udhaya Kumar
    G. Anantha Krishnan
    M. Velayutham Pillai
    P. Sakthivel
    Crystallography Reports, 2019, 64 : 1103 - 1107
12345