Abstract
The 1,3-dipolar cycloaddition reaction is one of the most rapid, and efficient protocols to access, and construct highly divergent heterocycle chiral auxiliaries. Free catalyst synthesis of spirooxindole scaffold incorporating sulphone moiety via one pot–three component reaction of 6-chloro-isatin, L-proline, and the phenylvinylsulphone as dienophile is presented. The new regioisomer and diastereomer was isolated by precipitation without the tedious purification step, and then characterized via NMR and single crystal X-ray diffraction analysis. Using Hirshfeld analysis, the analysis of molecular packing was performed. It depended mainly on strong O…H and N…H interactions, and weak H…H, C…H, and Cl…H interactions as well. DFT calculations were used to optimize the experimental X-ray structure, which was found well matched with the calculated one. Reactivity descriptors based on the energies of the highest occupied (HOMO) and lowest unoccupied (LUMO) molecular orbitals were calculated. Additionally, the donor–acceptor interactions which stabilized the system via σ–σ*, π→π*, n→σ* and n→π* electron delocalization processes were also computed using NBO calculations. The net interaction energies are 49.96, 235.38, 179.66 and 107.06 kJ/mol, respectively. Additionally, the calculated NMR chemical shifts correlated well with the experimental data (R2=0.99).
Highlights
The design and discovery of new and applicable materials are of great interest in the scientific community
Welwitindolinone A isonitrile is a marine employed this fascinating approach for the synthesis of a new spirooxindole having a sulphone alkaloid incorporating the spirooxindole motif structure and has been shown to have anti-fungal moiety in efficacy
The cycloadduct was obtained via reaction of phenylvinylsulphone as dienophile with the generated azomethine ylide by reaction of 6-chloro-isatin with the secondary amino acid (L-proline) under thermal condition
Summary
The design and discovery of new and applicable materials are of great interest in the scientific community. The best privileged chemotypes for sundry biological targets (Figure 1) This interesting scaffold has the in other hand, many as synthesized spirooxindole family[2]. Examples ofbeen naturally occurring significant biological activities Welwitindolinone A isonitrile is a marine employed this fascinating approach for the synthesis of a new spirooxindole having a sulphone alkaloid incorporating the spirooxindole motif structure and has been shown to have anti-fungal moiety in efficacy [6].enantioselective and diastereoselective fashion. 2. Materials and Methods significant biological activities The conformational constrained rings in the synthesized compound were investigated and assigned
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