One‐pot Regioselective Synthesis of Novel 1‐N‐Methyl‐spiro[2,3′]oxindole‐spiro[3,3″]‐1″‐N‐arylpyrrolidine‐2″,5″‐dione‐4‐arylpyrrolidines through Multicomponent 1,3‐Dipolar Cycloaddition Reaction of Azomethine Ylide

Abstract

in Wiley Online Library (wileyonlinelibrary.com).An atom economic and facile synthesis of novel dispiro-oxindole-pyrrolidines has been achieved via a three-component tandem cycloaddition of azomethine ylide generated in situ from isatin and sarcosine by decarboxylative condensation with N-aryl-3-benzylidene-pyrrolidine-2,5-dione derivatives as dipolarophiles. The salient features of synthetic procedure are characterized by the mild reaction conditions, high yields, high regioselectivity and stereoselectivity, one-pot procedure, and operational simplicity. This regioselectivity was assumed to be under the influence of π-π stacking interactions between the aromatic rings of azomethine ylide and N-aryl-3-benzylidene-pyrrolidine-2,5-diones that further control the exo-endo selectivity of the reaction 1,3-dipolar cycloaddition. The regiochemistry and structures of the cycloadducts were determined with spectroscopic data.

Selective Synthesis Dispiro[indoline‐3,2′‐pyrrolidine‐3′,3″‐quinoline] Derivatives and Spiro[imidazole‐4,3′‐quinoline] Derivatives via 1,3‐Dipolar Cycloaddition Reaction

“…From the calculations by using frontier orbital theory, we found that the endo cycloaddition intermediate has a binding energy with 42.884 Kcal/mol more negative value than the exo cycloaddition intermediate. Because the benzene ring of arylidine and the benzene ring of azomethine ylide are parallel to each other , so, the endo cycloaddition intermediate is more stable than the exo cycloaddition intermediate, and the dispiro 4 endo‐cycloaddition is formed while dispiro 5 exo‐cycloaddition not formed exo‐cycloaddition (Figs. and ).…”

Synthesis of 1-((4-methoxyphenyl)-3-alkynes)-1H-pyrrole-2,5-diones and functionalization to triazoles

“…Table 2 Sonogashira cross-coupling reaction between halomaleimide (6) and acetylenes (7a-k). Synthesis of 1-((4-methoxyphenyl)-3-alkynes)-1H-pyrrole-2,5-diones 5 anhydride and sodium acetate (Kaur et al, 2015) to get the cyclic maleimide 4. This cyclic maleimide was treated with bromine to obtain the dibromo intermediate 5, which further on treatment with triethylamine afforded the desired halomaleimide 6 (Rulev et al, 2013) Scheme 1.…”

Synthesis, Characterization and Biological Evaluation of 3'-Benzoyl-5'-(Furan-2-yl)-4'-Phenylspiro[Indoline-3,2'-Pyrrolidin]-2-One Derivatives and its Molecular Docking Studies

“…The aromatic and aliphatic C-H stretching absorption bands are observed in the region of 2853-3110 cm -1 . The observed imine and aromatic C-H stretching frequencies are the evidences for the formation of compounds 4a-g. 1 H NMR spectra of compounds 4a-g have been recorded in the solvent CDCl 3. The signals of the 1 H NMR spectra were assigned based on their positions, multiplicities and integral values.…”

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