Synthesis of Spirooxindoles through Cyclocondensation of Isatin and Cyclic 1,3‐Diones

Abstract

A simple, clean, and efficient method for the synthesis of spirooxindole derivatives via condensation of isatin with enolizable cyclic β-diketones has been developed. The use of water as a solvent allows avoiding the use of toxic organic solvents, which makes this reaction safe and environmentally friendly. The mechanism of the condensation reaction has been investigated using first-principles-based density functional theory calculations.

Dinuclear gold(I)‐N‐heterocyclic carbene complexes: Synthesis, characterization, and catalytic application for hydrohydrazidation of terminal alkynes

“…The use of explicit solvent reduced the barrier height significantly due to the formation of a six‐membered ring in place of the four‐membered ring, that reduced the ring strain and assisted the smooth hydrogen shuttle motion following a six‐membered ring and were known in the literature. [ 14a,17 ] This observation is thus emphasized the importance of explicit solvation in understanding the mechanism of such reactions. In the next step of the catalytic cycle, gold(I)‐NHC catalyst disassociates gradually from D" by breaking a strong bond with bond length 2.19 Å between Au and terminal alkene, thus forming a weak bond with the phenyl ring (bond length 2.40 Å) with an energy loss of 17.25 kcal mol −1 .…”

FeCl3 ⋅ 6H2O Mediated Sequential Oxidative Cleavage and Spiro Coupling of Peroxyoxindole with Cyclic‐1,3‐diketone/1‐Naphthol for the Synthesis of Spirooxindolo‐Xanthene Derivatives

“…Moreover, the spiro oxindoles comprise the core structure of many synthetic drugs and show characteristic biological activities [22] . Several approaches have been developed for spiro oxindoles synthesis by using cyclic‐1,3‐diketone and isatin derivatives in the presence of various catalysts such as HBF 4 supported nanoparticles, [23] SnCl 4 , [24] magnesium perchlorate, [25] zinc oxide, [26] ZnFe 2 O 4 , [27] B(HSO 4 ) 3 , [28] CAN, [29] and p ‐TSA (Scheme 1C) [30] . Recently, Lee and coworkers described the synthesis of xanthene‐bearing oxindole derivatives by spiro coupling of 1,4‐quinone derivatives with oxindoles in the presence of In‐(III) catalyst (Scheme 1D) [31] .…”

Synthesis of new functionalized thiazolo pyridine-fused and thiazolo pyridopyrimidine-fused spirooxindoles via one-pot reactions

“…Spirooxindoles are known as a subclass of indole that 3-carbon position of indole sharing in the constitution of spiroindole structures which makes them as core building blocks of many synthetic drugs [4,5], and natural functionalized organic compounds which raise their biological properties [6,7]. Spirooxindoles are valuable synthetic targets in organic chemistry and pharmacological research fields due to their remarkable biological properties including antimicrobial [8], antitumor [9], antidiabetic [10], potential antileukemic, local anesthetic [11], antifungal activities [12] and can also use as intermediates in synthetic steps for many types of medicinal precursors [13], e.g.…”

“…Spirooxindoles are valuable synthetic targets in organic chemistry and pharmacological research fields due to their remarkable biological properties including antimicrobial [8], antitumor [9], antidiabetic [10], potential antileukemic, local anesthetic [11], antifungal activities [12] and can also use as intermediates in synthetic steps for many types of medicinal precursors [13], e.g. spirotryprostatin A exhibit microtubule assembly inhibition while isopteropodine and pteropodine adjust the action of muscarinic serotonin receptors (Figure 1) [5,11]. Numerous reactions have been designed for the formation of diverse recognized spiro-based heterocycles by the classical cyclocondensation procedure [14,15,16].…”