1,3-Dipolar cycloaddition approach to novel dispiro[pyrazolidine-4,3′-pyrrolizidine-2′,3″-indoline]-2″,3,5-triones

Abstract

A simple and convenient 1,3-dipolar cycloaddition of non-stabilised azomethine ylides derived from isatins and L-proline, in a variety of different solvents, to ( Z)-4-arylidene-1-phenylpyrazolidine-3,5-diones as dipolarophiles afforded a series of novel dispiro[pyrazolidine-4,3′-pyrrolizidine-2′,3″-indoline]-2″,3,5-triones regioselectively and in good yields.

Synthesis, Optical and Electrochemical Properties of Novel Formazan Analogs Incorporated Fluorene Moiety

“…Therefore, the energies of HOMO and LUMO orbitals are employed as useful quantum chemical descriptors. Furthermore, as was demonstrated [45] that these two molecular orbitals were characterized by playing a considerable role in planning numerous chemical combinations, and found to be also accountable for charge transfer complexes [46–54] . Through this, electron affinity (EA) coupled with LUMO energy and ionization potential (IP) coupled with HOMO energy can be determined, and in which EA and IP describes the susceptibility of the molecule substance towards nucleophilic and electrophilic attack, respectively.…”

“…Moreover, HOMO and LUMO density are important of any reaction including molecules with donor and acceptor behavior, respectively. Frontier orbital densities were designed to provide more chemical information to depict the different atoms reactivity within the same molecule [46–54,58] . However, the electronegativity and hardness are useful descriptors and can improve the description about chemical behavior.…”

“…Furthermore, as was demonstrated [45] that these two molecular orbitals were characterized by playing a considerable role in planning numerous chemical combinations, and found to be also accountable for charge transfer complexes. [46][47][48][49][50][51][52][53][54] Through this, electron affinity (EA) coupled with LUMO energy and ionization potential (IP) coupled with HOMO energy can be determined, and in which EA and IP describes the susceptibility of the molecule substance towards nucleophilic and electrophilic attack, respectively. It also involves the hard/soft electrophiles and nucleophiles concept, related directly with the corresponding HOMO and LUMO orbitals energies.…”

Green synthetic investigation and spectral characterization of some spiro pyrazolidine‐based heterocycles with potential biological activity

“…Here a modified method was employed to improve the isolated yield of the desired compounds compared with the previous work . Heating of 3 with different carbonyl compounds under solvent‐free condition gave excellent yield of 4‐alkylidene ( 4a and 4b ) or 4‐arylidene derivatives ( 4c‐h ) (chalcone derivatives) (Scheme ) compared with reported literature . 4‐(2′‐Methoxylbenzylidene)‐1‐phenyl‐3,5‐pyrazolidinedione ( 4e ) was ascertained through spectral analysis as 1 HNMR, 13 CNMR, DEPT‐135, COSY, HSQC, and HMBC.…”

“…[20,22] Heating of 3 with different carbonyl compounds under solvent-free condition gave excellent yield of 4-alkylidene (4a and 4b) or 4-arylidene derivatives (4c-h) (chalcone derivatives) (Scheme 2) compared with reported literature. [25][26][27][28][29][30][31][32][33][34][35][36][37][38][39] 4-(2 0 -Methoxylbenzylidene)-1-phenyl-3,5-pyrazolidinedione (4e) was ascertained through spectral analysis as 1 HNMR, 13 CNMR, DEPT-135, COSY, HSQC, and HMBC. The 2D NMR analysis was in agreement with the proposed structure.…”