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.
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页码：388 / 393
页数：6
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[21]   Synthesis, Crystal Structure and Antifungal Activity of 4-(5-((2,4-Dichlorobenzyl)thio)-4-phenyl-4H-1,2,4-triazol-3-yl)pyridine [J].
Yang Ming-Yan ;
Zhao Wen ;
Liu Xing-Hai ;
Tan Cheng-Xia ;
Weng Jian-Quan .
CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2015, 34 (02) :203-207
[22]   Synthesis, Crystal Structure and Insecticidal Activity of N-(pyridin-2-ylmethyl)-1-phenyl-1,4,5,6,7,8-hexahydrocyclohepta [c]pyrazole-3-carboxamide [J].
Deng Xi-Le ;
Zhou Xiao-Mao ;
Wang Zan-Yong ;
Rui Chang-Hui ;
Yang Xin-Ling .
CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2018, 37 (04) :551-556
[23]   Design,synthesis and biological evaluation of 1,4-dihydrothieno[3′,2′:5,6]thiopyrano[4,3-c]pyrazole-3-carboxylic amide derivatives as potential estrogen receptor antagonists [J].
Diwa Koirala .
Chinese Chemical Letters, 2011, 22 (03) :256-259
[24]   Design, synthesis and biological evaluation of 1,4-dihydrothieno[3′,2′:5,6]thiopyrano[4,3-c]pyrazole-3-carboxylic amide derivatives as potential estrogen receptor antagonists [J].
Sun, Rui ;
Song, Jing ;
Liu, Si Jie ;
Zhao, Hui ;
Yan, Chun Li ;
Zhang, Ai Jun ;
Koirala, Diwa ;
Li, Da Wei ;
Hu, Chun .
CHINESE CHEMICAL LETTERS, 2011, 22 (03) :256-259
[25]   Synthesis, Crystal Structure and Antitumor Activities of Ethyl (R)-2-(Biphenyl-4-carbonyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-carboxylate [J].
Hu Chun-Hong ;
Wei Dui-Dui ;
Zhao Jing-Si ;
Hu Min-Min ;
Qi Sheng-Xiao ;
Sun Xiao-Fei ;
He Dian .
CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2018, 37 (01) :91-96
[26]   Synthesis, Crystal Structure, and Biological Activity of 4-Chlorobenzaldehyde (2-trifluoromethylTrifluoromethyl-5,6,7,8-tetrahydrobenzo[4 ,5]-thieno[2,3-d]pyrimidin-4-yl)hydrazone Monohydrate [J].
杨平 ;
王艳 ;
段正超 ;
邵 宇 ;
聂光华 ;
宋新建 ;
田大听 .
结构化学, 2013, 32 (07) :1023-1030
[27]   Crystal structure of 2-methylamino-3-nitro-4-p-tolylpyrano[3,2-c] chromen-5(4H)-one [J].
Govindaraj, J. ;
AaminaNaaz, Y. ;
Kamalraja, Jayabal ;
Perumal, Paramasivam T. ;
SubbiahPandi, A. .
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2015, 71 :O158-+
[28]   Synthesis, Crystal Structure, and Biological Activity of 4-Chlorobenzaldehyde (2-Trifluoromethyl-5,6,7,8-tetrahydrobenzo[4,5]-thieno[2,3-d]pyrimidin-4-yl)hydrazone Monohydrate [J].
Yang Ping ;
Wang Yan ;
Duan Zheng-Chao ;
Shao Yu ;
Nie Guang-Hua ;
Song Xin-Jian ;
Tian Da-Ting .
CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2013, 32 (07) :1023-1030
[29]   Synthesis and anti-inflammatory activity of N-substituted 4-aryl-2-[(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)amino]-4-oxobut-2-enamides [J].
Gorbunova, I. A. ;
Okoneshnikova, E. A. ;
Makhmudov, R. R. ;
Shadrin, V. M. ;
Silaichev, P. S. ;
Shipilovskikh, S. A. ;
Shipilovskikh, D. A. .
RUSSIAN CHEMICAL BULLETIN, 2024, 73 (09) :2758-2764
[30]   Synthesis and Crystal Structure of 4-[5-(2-Bromophenyl)-1,3,4-thiadiazol-2-ylthio]-2-(trifluoromethyl)thieno[2,3-d]pyrimidine [J].
Yang, Ping ;
Gao, Hui ;
Nie, Yao ;
Zeng, Zhen ;
Zhao, Jinshun ;
Song, Xinjian .
ADVANCES IN MATERIALS AND MATERIALS PROCESSING IV, PTS 1 AND 2, 2014, 887-888 :703-+
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