Unknown

Dataset Information

0

Unprecedented Regio- and Stereoselective Synthesis of Pyrene-Grafted Dispiro[indoline-3,2'-pyrrolidine-3',3?-indolines]: Expedient Experimental and Theoretical Insights into Polar [3 + 2] Cycloaddition.

ABSTRACT: A series of dispiro[indoline-3,2'-pyrrolidine-3',3?-indolines] was synthesized via a multicomponent polar [3 + 2] cycloaddition (32CA) reaction of isatin derivatives, sarcosine and (E)-3-(2-oxo-2-(pyren-1-yl)ethylidene)indolin-2-one derivatives. The regio- and stereochemistries of the cycloadducts were established on the basis of one-dimensional (1D) (1H-, 13C-, 13C-CRAPT NMR) and two-dimensional (2D) homonuclear and heteronuclear correlation NMR spectrometry experiments (1H-1H gDQFCOSY, 13C-1H-HSQCAD, 13C-1H-HMBCAD, 1H-1H-ROESYAD). The molecular mechanism and regio- and stereoselectivities of the cycloaddition (CA) reaction have been investigated utilizing a density functional theory (DFT) method and were thoroughly explained based on the transition-state stabilities and global/local electrophilicity/nucleophilicity reactivity indices of the reactants.

SUBMITTER: Hussein EM 

PROVIDER: S-EPMC7513337 | biostudies-literature | 2020 Sep

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Unprecedented Regio- and Stereoselective Synthesis of Pyrene-Grafted Dispiro[indoline-3,2'-pyrrolidine-3',3″-indolines]: Expedient Experimental and Theoretical Insights into Polar [3 + 2] Cycloaddition.

Hussein Essam M EM   El Guesmi Nizar N   Moussa Ziad Z   Pal Uttam U   Pal Samir K SK   Saha Dasgupta Tanusri T   Ahmed Saleh A SA  

ACS omega 20200914 37

A series of dispiro[indoline-3,2'-pyrrolidine-3',3″-indolines] was synthesized via a multicomponent polar [3 + 2] cycloaddition (32CA) reaction of isatin derivatives, sarcosine and (<i>E</i>)-3-(2-oxo-2-(pyren-1-yl)ethylidene)indolin-2-one derivatives. The regio- and stereochemistries of the cycloadducts were established on the basis of one-dimensional (1D) (<sup>1</sup>H-, <sup>13</sup>C-, <sup>13</sup>C-CRAPT NMR) and two-dimensional (2D) homonuclear and heteronuclear correlation NMR spectrome  ...[more]

Similar Datasets

Unknown 4'-(4-Methoxy-phen-yl)-1,1',1''-trimethyl-dispiro-[indoline-3,2'-pyrrolidine-3',3''-pyrrolidine]-2,2'',5''-trione.
| S-EPMC2969413 | biostudies-literature
Unknown Selective construction of dispiro[indoline-3,2'-quinoline-3',3''-indoline] and dispiro[indoline-3,2'-pyrrole-3',3''-indoline] via three-component reaction.
| S-EPMC10478003 | biostudies-literature
Unknown Synthesis and molecular modeling studies of cholinesterase inhibitor dispiro[indoline-3,2'-pyrrolidine-3',3''-pyrrolidines].
| S-EPMC9054546 | biostudies-literature
Unknown 1'-Methyl-4'-phenyl-2''-sulfanylidene-dispiro-[indoline-3,2'-pyrrolidine-3',5''-1,3-thia-zolidine]-2,4''-dione.
| S-EPMC3275027 | biostudies-literature
Unknown 5''-Benzyl-idene-5-chloro-1',1''-dimethyl-4'-phenyl-dispiro-[indoline-3,2'-pyrrolidine-3',3''-piperidine]-2,4''-dione.
| S-EPMC4029213 | biostudies-literature
Unknown 1'-Methyl-4'-phenyl-dispiro-[chromane-3,3'-pyrrolidine-2',3''-indoline]-2,2''-dione.
| S-EPMC3297956 | biostudies-literature
Unknown An Expedient Regio- and Diastereoselective Synthesis of Hybrid Frameworks with Embedded Spiro[9,10]dihydroanthracene [9,3']-pyrrolidine and Spiro[oxindole-3,2'-pyrrolidine] Motifs via an Ionic Liquid-Mediated Multicomponent Reaction.
| S-EPMC6332494 | biostudies-literature
Unknown 5-Chloro-5''-(4-chloro-benzyl-idene)-4'-(4-chloro-phen-yl)-1''-ethyl-1'-methyl-dispiro-[indoline-3,2'-pyrrolidine-3',3''-piperidine]-2,4''-dione.
| S-EPMC4029214 | biostudies-literature
Unknown Facile access to regio- and stereoselective synthesis of highly functionalized spiro[indoline-3,2'-pyrrolidines] incorporating a pyrene moiety: experimental, photophysical and theoretical approach.
| S-EPMC9081859 | biostudies-literature
Unknown Methyl 5''-chloro-1',1''-dimethyl-2,2''-dioxodi-spiro-[indoline-3,2'-pyrrolidine-3',3''-indoline]-4'-carboxyl-ate.
| S-EPMC3684914 | biostudies-literature