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

Essam M. Hussein, Nizar El Guesmi, Ziad Moussa, Uttam Pal, Samir K. Pal, Tanusri Saha Dasgupta, Saleh A. Ahmed

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)24081-24094
Number of pages14
JournalACS Omega
Volume5
Issue number37
DOIs
Publication statusPublished - Sep 22 2020

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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