abstract
Spiro compounds are a class of naturally occurring organic molecules with a wide broad of applica-tions in several fields, mainly in medicinal chemistry. Spirooxindoles have been considered by the sci-entific community as scaffolds for applications under medicinal purposes, namely as anticancer, antiviral, or antimicrobial agents. Due to this fact, the synthesis of spirocompounds, namely spirooxindoles is a hot topic in organic chemistry field. Herein, we report a catalyst-less synthesis of new spiro[indoline-3,1'-pyrazolo[1,2-a]pyrazoles] via 1,3-dipolar cycloadditions of isatin N,N'-cyclic azomethine imines with dimethylacetylenedicarboxylate (DMAD). A "library" of cycloadducts were obtained in good yields (59- 77%) and were characterized by NMR spectral analyses and further confirmed by the single-crystal X-ray diffraction analysis of all the cycloadducts.(c) 2022 Elsevier B.V. All rights reserved.
keywords
AZOMETHINE IMINE 1,3-DIPOLE; DESIGN; POTENT
subject category
Chemistry
authors
Abdelmouna, K; Laghchioua, F; Paz, FAA; Mendes, RF; Moura, NMM; Faustino, MAF; Cavaleiro, JAS; Rodi, YK; Rakib, E; Neves, MGPMS
our authors
Filipe Alexandre Almeida Paz
Principal Researcher
Ricardo Faria Mendes
Junior Researcheracknowledgements
The authors thank the University of Aveiro, FCT/MCTES for their financial support to the LAQV-REQUIMTE (UIDB/50006/2020) through national funds and, where applicable, co-financed by the FEDER, within the PT2020 Partnership Agreement, and to the Portuguese NMR Network. This work was developed within the scope of the project CICECO -Aveiro Institute of Materials (UIDB/50 011/2020, UIDP/50011/2020 & LA/P/0 0 06/2020) financed by national funds through the FCT/MEC (PIDDAC). The authors also thank the Sultan Moulay Slimane University and the Transnational cooperation programs, FCT-CNRST (Morocco), for financial assistance (2019-2022). NMM Moura, thanks his research contract (CDL-CTTRI-048-88-ARH/2018) which is funded by national funds (OE), through FCT -Fundacao para a Ciencia e a Tecnologia, I.P., in the scope of the framework contract foreseen in numbers 4, 5 and 6 of the article 23, of the Law Decree 57/2016, of August 29, changed by Law 57/2017, of July 19. RFM gratefully acknowledges FCT for a Junior Research Position (CEECIND/00553/2017).