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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

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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]

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