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
来源：
JOURNAL OF HETEROCYCLIC CHEMISTRY | 2018年 / 55卷 / 02期
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
[51]   Three-component synthesis and anticancer evaluation of polycyclic indenopyridines lead to the discovery of a novel indenoheterocycle with potent apoptosis inducing properties [J].
Manpadi, Madhuri ;
Uglinskii, Pavel Y. ;
Rastogi, Shiva K. ;
Cotter, Karen M. ;
Wong, Yin-Shan C. ;
Anderson, Lisa A. ;
Ortega, Amber J. ;
Van Slambrouck, Severine ;
Steelant, Wim F. A. ;
Rogelj, Snezna ;
Tongwa, Paul ;
Antipin, Mikhail Yu. ;
Magedov, Igor V. ;
Kornienko, Alexander .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (23) :3865-3872
[52]   Molecular Design of Pyrazolo[3,4-d]pyridazines [J].
Matiichuk, V. S. ;
Potopnyk, M. A. ;
Obushak, N. D. .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 44 (09) :1352-1361
[53]   Synthesis and reactions of 3-(3-ethoxycarbonyl-1-phenyl-1H-pyrazol-4-yl)propenic acid [J].
Matiichuk, V. S. ;
Potopnyk, M. A. ;
Obushak, N. D. .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 45 (05) :712-718
[54]   A Simple and Efficient Synthesis of Ethyl 1-Aryl-4-formyl-1H-pyrazole-3-carboxylates [J].
Matiychuk, Vasyl S. ;
Potopnyk, Mykhaylo A. ;
Obushak, Mykola D. .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2013, 50 :E43-E47
[55]   Recent developments in the chemistry of pyrazolo[4,3-c]quinolines [J].
Mekheimer, Ramadan A. ;
Ahmed, Eltaib A. ;
Sadek, Kamal U. .
TETRAHEDRON, 2012, 68 (06) :1637-1667
[56]   Regioselective Synthesis, Antimicrobial Evaluation and QSAR Studies of Some 3-Aryl-1-heteroarylindeno[1,2-c]pyrazol-4(1H)-ones [J].
Mor, Satbir ;
Mohil, Rajni ;
Nagoria, Savita ;
Kumar, Ashwani ;
Lal, Kashmiri ;
Kumar, Devinder ;
Singh, Virender .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (02) :1327-1341
[57]   First Copper-Catalyzed Intramolecular Amidation in Substituted 4-Iodopyrazoles Leading to the Synthesis of Pyrazolo[4,3-b]-pyridin-5-ones [J].
Nag, Somnath ;
Nayak, Maloy ;
Batra, Sanjay .
ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (16) :2715-2723
[58]   Natural Products Containing a Nitrogen-Nitrogen Bond [J].
Blair, Lachlan M. ;
Sperry, Jonathan .
JOURNAL OF NATURAL PRODUCTS, 2013, 76 (04) :794-812
[59]   Copper-Catalyzed Cascade Reaction of 4-Iodopyrazole Derivatives with Amidines for the Synthesis of Pyrazolo[4,3-d]pyrimidine Derivatives [J].
Nayak, Maloy ;
Rastogi, Neeraj ;
Batra, Sanjay .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (07) :1360-1366
[60]   Synthesis of celecoxib via 1,3-dipolar cycloaddition [J].
Oh, Lynette M. .
TETRAHEDRON LETTERS, 2006, 47 (45) :7943-7946
12345678910