4-Formyl-Pyrazole-3-Carboxylate: A Useful Aldo-X Bifunctional Precursor for the Syntheses of Pyrazole-fused/Substituted Frameworks

被引:40
作者
Devi, Nisha [1 ]
Shankar, Ravi [2 ]
Singh, Virender [1 ]
机构
[1] Dr BR Ambedkar Natl Inst Technol, Dept Chem, Jalandhar 144011, India
[2] CSIR Indian Inst Integrat Med, Bioorgan Chem Div, Jammu 180001, India
关键词
1,3-DIPOLAR CYCLOADDITION REACTIONS; INFLAMMATORY-ANTIMICROBIAL AGENTS; O-ALKYNYL ALDEHYDES; ONE-POT SYNTHESIS; BIOLOGICAL EVALUATION; BETA-CARBOLINE; NITRILIMINE CYCLOADDITION; REGIOSELECTIVE SYNTHESIS; HETEROGENEOUS CATALYST; MOLECULAR HYBRIDS;
D O I
10.1002/jhet.3045
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Pyrazole, a privileged class of heterocyclic compounds, constitute an interesting template for medicinal chemistry and is represented by several commercial drugs like Sildenafil, Zometapin, Celebrex, and Rimonabant. The presence of two functionalities with different reactivity in pyrazole moiety may open new avenues for insertion of diversity in pyrazole frameworks which may be of high medicinal significance. Ethyl 4-formyl-1H-pyrazole-3-carboxylate is a potential Aldo-X bifunctional building block (AXB3) which may be explored for generating complex pyrazole based molecular frameworks by using various organic transformations. The present manuscript is assimilation of literature pertaining to the synthesis and application of ethyl 4-formyl-1H-pyrazole-3-carboxylates and similar AXB3 for the development of pyrazole substituted and fused derivatives.
引用
收藏
页码:373 / 390
页数:18
相关论文
共 94 条
[61]   Synthesis of sildenafil analogues from anacardic acid and their phosphodiesterase-5 inhibition [J].
Paramashivappa, R ;
Kumar, PP ;
Rao, PVS ;
Rao, AS .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2002, 50 (26) :7709-7713
[62]  
PAWAR RA, 1989, J INDIAN CHEM SOC, V66, P203
[63]   Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: Identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide (SC-58635, Celecoxib) [J].
Penning, TD ;
Talley, JJ ;
Bertenshaw, SR ;
Carter, JS ;
Collins, PW ;
Docter, S ;
Graneto, MJ ;
Lee, LF ;
Malecha, JW ;
Miyashiro, JM ;
Rogers, RS ;
Rogier, DJ ;
Yu, SS ;
Anderson, GD ;
Burton, EG ;
Cogburn, JN ;
Gregory, SA ;
Koboldt, CM ;
Perkins, WE ;
Seibert, K ;
Veenhuizen, AW ;
Zhang, YY ;
Isakson, PC .
JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (09) :1347-1365
[64]   A review of recent progress (2002-2012) on the biological activities of pyrazoles [J].
Perez-Fernandez, Ruth ;
Goya, Pilar ;
Elguero, Jose .
ARKIVOC, 2014, :233-293
[65]   Greener and rapid access to bio-active heterocycles: room temperature synthesis of pyrazoles and diazepines in aqueous medium [J].
Polshettiwar, Vivek ;
Varma, Rajender S. .
TETRAHEDRON LETTERS, 2008, 49 (02) :397-400
[66]  
Potopnyk M., 2008, SER KHIM, V49, P96
[67]  
Potopnyk M. A., 2009, UKRAINICA BIOORGANIC, V7, P42
[68]   Design, synthesis and biological evaluation of (1,3-diphenyl-1H-pyrazol-4-yl) methyl benzoate derivatives as potential BRAFV600E inhibitors [J].
Qin, Ya-Juan ;
Xing, Man ;
Zhang, Ya-Liang ;
Makawana, Jigar A. ;
Jiang, Ai-Qin ;
Zhu, Hai-Liang .
RSC ADVANCES, 2014, 4 (95) :52702-52711
[69]   Molecular iodine: a green and inclusive catalyst for the synthesis of highly functionalized 1,3,5-trisubstituted pyrazoles in aqueous medium [J].
Rai, Pratibha ;
Srivastava, Madhulika ;
Singh, Jaya ;
Singh, Jagdamba .
RSC ADVANCES, 2014, 4 (02) :779-783
[70]   Aldo-X Bifunctional Building Blocks for the Synthesis of Heterocycles [J].
Ravichandiran, Palanisamy ;
Lai, Bingbing ;
Gu, Yanlong .
CHEMICAL RECORD, 2017, 17 (02) :142-183