Recent Strategies in the Synthesis of Spiroindole and Spirooxindole Scaffolds

Expeditious entry into carbocyclic and heterocyclic spirooxindoles

“…14 Recently, Nasri et al reviewed the chemistry of spiroindoles and spirooxindoles and discussed methods and pharmacological strategies based on the type and ring size of the spirocycle that is fused to indole or oxindole. 15 Different-sized rings com-Fig. 1 The number of published 'spirooxindole' articles in journals.…”

“…14 Recently, Nasri et al reviewed the chemistry of spiroindoles and spirooxindoles and discussed methods and pharmacological strategies based on the type and ring size of the spirocycle that is fused to indole or oxindole. 15 Different-sized rings comprising carbocycles and heterocycles spirofused to oxindoles were covered. Further, Boddy and Bull delineated an exhaustive approach to the synthesis and applications of spirocyclic oxindoles possessing three to eight-membered carbocyclic and heterocyclic rings.…”

Efficient Synthesis of 2,3′-Spirobi (Indolin)-2′-Ones and Preliminary Evaluation of Their Damage to Mitochondria in HeLa Cells

“…( Gounder et al, 2016 ) Their notable biological activities prompted the development of numerous strategies toward the syntheses of 3,3′-pyrrolidinyl-spirooxindole moiety. ( Cao and Zhou, 2015 ; He et al, 2020 ; Liu X. et al, 2020 ; Nakamura et al, 2020 ; Reddy et al, 2020 ; Bortolami et al, 2021 ; Nasri et al, 2021 ; Saranya et al, 2021 ) Nevertheless, the construction of the structurally similar spirobi (indolin) frameworks (Skeleton B, Figure 1 bottom left) has been less studied, and until now, only two synthetic methods have been reported for the synthesis of 2,3′-spirobi (indolin)-2′-ones. ( Gui et al, 2019 ; Wang et al, 2019 ) In 2019, Shi and co-workers pioneered the (4 + 1) annulation of 3-isothiocyanato oxindoles and aza- o -quinone methides, affording the corresponding condensed products in two steps.…”

Easy Access to Indole‐based Bi‐Sulfurylate‐Heterocyclic Scaffolds

“…Furthermore, the study of the mechanistic aspects involved in the synthesis of derivatives A suggested that a structural modification of the starting indoline 2‐thiones 2 could trigger a different cyclization that leads to the formation of new and interesting 3,3‐dimethyl‐3′ H ‐spiro‐indoline‐2,2′‐thiazol derivatives 5 (Figure 2). Spiro compounds represent an important class of organic frameworks and natural products manifesting numerous pharmacological activities; among them, the anticancer properties of spiro compounds have prompted medicinal chemists to investigate new spiro‐derivatives with significantly improved pharmacodynamic and pharmacokinetic profile [28] . Then, also the development of new and simply strategies devoted to their preparation are topics of great relevance.…”

“…Spiro compounds represent an important class of organic frameworks and natural products manifesting numerous pharmacological activities; among them, the anticancer properties of spiro compounds have prompted medicinal chemists to investigate new spiro-derivatives with significantly improved pharmacodynamic and pharmacokinetic profile. [28] Then, also the development of new and simply strategies devoted to their preparation are topics of great relevance. Here, the investigations on the synthesis of both unprecedented 4-((1H-indol-2-yl)thio)-5-oxo-4,5-dihydro-1H-pyrazoles 4 and 3,3-dimethyl-3'H-spiro-indoline-2,2'-thiazole derivatives 5 are described (Figure 2).…”