In the continuation of efforts to modify the structure of our novel DP-IV inhibitors, a series of pyrazolidine derivatives with heteroaryl urea was synthesized and evaluated for their ability to inhibit dipeptidyl peptidase IV (DP-IV).
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Asymmetric Synthesis of Optically Active Pyrazolidines or Pyrazoline Derivatives via Ni(II)-Bipyridine-,'-dioxide Complexes.
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School of Chemistry and Chemical Engineering/State Key Laboratory Incubation Base for Green Processing of Chemical Engineering, Shihezi University, Shihezi, Xinjiang 832003, China.
Easily obtainable and efficient chiral -symmetric bipyridine-,'-dioxide ligands with Ni(OTf) were developed for application in catalyzing [3 + 2] cycloaddition reactions to synthesize optically active fused pyrazolidines or pyrazoline derivatives featuring three contiguous stereogenic centers by employing azomethine imines and α,β-unsaturated 2-acyl imidazoles, affording the corresponding adducts with the opposite configuration compared to previous synthetic products in 80-98% yields with 28-99% ee and >20:1 dr. In addition, subsequent amplification experiments and derivative transformations of the product further demonstrated the efficient catalytic performance of the catalyst Ni(II)-bipyridine-,'-dioxide complexes and the practicality of this synthesis methodology.
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PLoS One
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Research Department of Chemistry, Nehru Memorial College (Affiliated Bharathidasan University), Puthanampatti, Tamilnadu, India.
The objective of this study was to develop pyrazolidine-3,5-dione derivatives with potential as environmentally friendly pesticides for pest control, specifically focusing on their efficacy as larvicidal agents. A novel one-pot synthesis of multicomponent pyrazolidine-3,5-dione derivatives (1a-m) was accomplished via the grindstone method using Cu(II)tyrosinase enzyme as a catalyst under mild reaction conditions, yielding 84%-96%. The synthesised derivatives (1a-m) were characterized using various spectroscopic methods (mass spectrometry, elemental analysis, FT-IR, and 1H and 13C NMR).
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Org Lett
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Department of Chemistry, Indian Institute of Science Education and Research (IISER) Bhopal, Bhopal By-pass Road, Bhauri, Bhopal 462066, India.
Herein, we report an intriguing cascade strategy for synthesizing optically active fused pyrazolidines featuring three contiguous stereogenic centers. The formyl-tethered enones are templates for the developed umpolung reactivity, showcasing diverse substrate adaptability with various arylhydrazines. The chiral phosphoric acid catalyst offers stereochemical guidance, forming the fused pyrazolidines with commendable to excellent stereoselectivities.
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Chemistry
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Department of Organic Chemistry, University of Geneva, Quai Ernest Ansermet 30, 1211, Geneva 4, Switzerland.
Thanks to the ability of diazo derivatives to react either as 1,3-dipoles and as carbenes after dinitrogen extrusion, combinations of oxa or aza benzonorbornadienes and diazomalonates afford polycyclic pyrazolidines via a three-step sequence of (i) a highly diastereoselective [3+2]-cycloaddition, (ii) a CpRu-catalyzed carbene addition, and (iii) a second dipolar cycloaddition. Of importance, step (II) represents a unique access to novel bench-stable N,N-cyclic azomethine imines, which behave as effective 1,3-dipoles in combination with electron-poor dipolarophiles. Each step proceeds efficiently and the 3-step process can be performed in one-pot to yield a polycyclic pyrazolidine in excellent overall yield (90 %).
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Department of Fire Protection Engineering, China Fire and Rescue Institute, Beijing 102202, P. R. of China.
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