Tetrahydroindeno[1′,2′:4,5]pyrrolo[1,2-a]imidazol-5(1H)-ones as Novel Neonicotinoid Insecticides: Reaction Selectivity and Substituent Effects on the Activity Level

Abstract

Tetraheterocyclic tetrahydroindeno[1',2':4,5]pyrrolo[1,2-a]imidazol-5(1H)-one derivatives as novel neonicotinoid candidates were designed and prepared by selective etherification, chlorination and esterification of ninhydrin-heterocyclic ketene aminals adducts. Some of the designed compounds showed excellent insecticidal activity against cowpea aphids (Aphis craccivora), brown planthopper (Nilaparvata lugens), and armyworm (Mythimna separata). In particular, the activity against armyworm (Mythimna separata) improved a lot in contrast with that of imidacloprid and cycloxaprid. The research here provides a novel neonicotinoid chemotype for further development.

A Simple and Efficient Synthesis of Highly Substituted Indeno[1,2-b]pyrrole and Acenaphtho[1,2-b]pyrrole Derivatives by Tandem Three-Component Reactions

“…Polysubstituted pyrroles are widely employed as versatile building blocks in synthetic organic chemistry [ 1 , 2 , 3 , 4 ] because of their presence in numerous natural products and drug molecules, and because they exhibit different pharmacological applications including anti-tuberculosis, anti-oxidation, antibacterial, anti-inflammatory, and antitumor properties, among others [ 5 , 6 , 7 ]. Among them, indeno[1,2- b ]pyrroles ( Figure 1 A,B) are heterocycles of great importance because they can be used as antiviral agents, insecticides, herbicides and human protein kinase CK2 inhibitors [ 8 , 9 , 10 ]. Moreover, acenaphtho[1,2- b ]pyrroles ( Figure 1 C), as important polycyclic fused compounds, can also be employed as potent and selective inhibitors of fibroblast growth factor receptor 1 (FGFR-1), novel Bcl-2 inhibitors, and as a valuable Mcl-1 inhibitor [ 11 , 12 , 13 , 14 ].…”

Facile Route to the Synthesis of 1,3-Diazahetero-Cycle-Fused [1,2-a]Quinoline Derivatives via Cascade Reactions

“…Heterocyclic ketene aminals (HKAs) have been widely used as a type of versatile building blocks to construct various fused heterocyclic compounds including quinolones, , isoquinolin-1-imine, indoles, indolin-2-ones, , isocoumarins, pyridines, − pyrroles, and so forth − Many of these compounds have a wide variety of biological activities, such as antitumor, − herbicidal, pesticidal, , antileishmanial, and antibacterial. , Therefore, it is vital and urgent to develop a green synthetic methodology with benign conditions and straight-forward post-treatment for the synthesis of quinoline derivatives by construction of CC and C–N bonds through the one-step cascade reaction.…”

One-Pot Synthesis of Highly Functionalized Bicyclic Imidazopyridinium Derivatives in Ethanol

“…N -Benzyl nitro ketene aminals (NBNKAs 2 ) (Scheme ) belong to the heterocyclic ketene aminals (HKAs). − NBNKAs are versatile building blocks that have been widely used to construct molecularly diverse heterocyclic compounds − such as quinolones, pyridines, pyrroles, and spirooxindoles. , …”