TY - JOUR
T1 - Unprecedented Regio- And stereoselective synthesis of pyrene-grafted dispiro[indoline-3,2'-pyrrolidine-3',3'-indolines]
T2 - Expedient experimental and theoretical insights into polar [3 + 2] cycloaddition
AU - Hussein, Essam M.
AU - El Guesmi, Nizar
AU - Moussa, Ziad
AU - Pal, Uttam
AU - Pal, Samir K.
AU - Saha Dasgupta, Tanusri
AU - Ahmed, Saleh A.
N1 - Publisher Copyright:
Copyright © 2020 American Chemical Society.
PY - 2020/9/22
Y1 - 2020/9/22
N2 - 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.
AB - 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.
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U2 - 10.1021/acsomega.0c03510
DO - 10.1021/acsomega.0c03510
M3 - Article
AN - SCOPUS:85092594382
SN - 2470-1343
VL - 5
SP - 24081
EP - 24094
JO - ACS Omega
JF - ACS Omega
IS - 37
ER -