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

doi:10.1021/acsomega.0c03510

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

ACS Omega. 2020 Sep 14;5(37):24081-24094. doi: 10.1021/acsomega.0c03510. eCollection 2020 Sep 22.

Authors

Essam M Hussein^{1

2}, Nizar El Guesmi^{1

3}, Ziad Moussa⁴, Uttam Pal⁵, Samir K Pal⁶, Tanusri Saha Dasgupta⁷, Saleh A Ahmed^{1

2}

Affiliations

¹ Department of Chemistry, Faculty of Applied Science, Umm Al-Qura University, 21955 Makkah, Saudi Arabia.
² Department of Chemistry, Faculty of Science, Assiut University, 71516 Assiut, Egypt.
³ Département de Chimie, Faculté des Sciences de Monastir, Avenue de l'Environnement, 5019 Monastir, Tunisia.
⁴ Department of Chemistry, College of Science, United Arab Emirates University, P.O. Box 15551, Al Ain, United Arab Emirates.
⁵ Technical Research Centre, S.N. Bose National Centre for Basic Sciences, Block JD, Sector III, Salt Lake, Kolkata 700106, India.
⁶ Department of Chemical, Biological & Macromolecular Sciences, S.N. Bose National Centre for Basic Sciences, JD Block, Sector III, Salt Lake, Kolkata 700106, India.
⁷ Department of Condensed Matter Physics and Material Sciences, S.N. Bose National Centre for Basic Sciences, Block JD, Sector III, Salt Lake, Kolkata 700106, India.

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.