An expedient approach for the synthesis of dispiropyrrolidine bisoxindoles, spiropyrrolidine oxindoles and spiroindane-1,3-diones through 1,3-dipolar cycloaddition reactions

Molecular diversity of spirooxindoles. Synthesis and biological activity

“…doles 188-190 were synthesized using isatylidene malononitrile 99, 2-(1H -indole-3-carbonyl)-3-phenyl-acrylonitrile 186 and 2-(1,3-dioxo-indan-2-ylidene)-malononitrile 187 as dipolarophiles, respectively (Scheme 46)[103]. The observed endo-regioisomers 188-190 are more favorable due to the secondary orbital interaction, which is not possible in the exo-transition state.2-Oxo-(2H )-acenaphthylen-1-ylidene-malonodinitrile 191 and 2-fluoren-9-ylidene-malonodinitrile 192 have been investigated for the first time as dipolarophiles in the 1,3-dipolar cycloaddition reaction with the azomethine ylides generated in situ from N-substituted isatins 114, and sarcosine 63 to afford novel dispiroheterocycles 193 and 194 (Scheme 47)[104].Fluorene derivatives, such as 9-arylidine-fluorene 195 can be utilized in the regioselective synthesis of novel dispiro[pyrrolo/pyrrolizidino] ring systems 196 by the cycloaddition to the azomethine ylides generated by a decarboxylative route from sarcosine 63/L-proline 74 and isatin 114 using different methodologies (Scheme 48)[105].…”

Ultrasound-assisted, ZnBr2-catalyzed regio- and stereoselective synthesis of novel 3,3′-dispiropyrrolidine bisoxindole derivatives via 1,3-dipolar cycloaddition reaction of an azomethine ylide

“…General procedure for synthesis of the 3,3′-dispiropyrrolidine bisoxindole (8a-l). A mixture of (E)-3-benzylideneindolin-2-one 7a-l (1 mmol), isatin (147 mg, 1 mmol), sarcosine (89 mg, 1 mmol) and anhydrous ZnBr2 (20%, 45 mg, 0.2 mmol) in methanol (10 mL) was sonicated for 30 minute at room temperature (25)(26)(27)(28)(29)(30) o C). After completion of the reaction as monitored by TLC, the mixture was poured in ice cold water and the precipitates were filtered and air dried.…”

“…The challenges associated with the synthesis of spiro-or dispiro-heterocycles containing the 3,3′-pyrrolidinyl-spirooxindole core have made them the subject of several elegant synthetic investigations. [22][23][24][25][26][27][28][29][30][31][32] Ultrasound irradiation has increasingly been used as a powerful tool for the preparation of organic molecules either in homogeneous or in heterogeneous liquid reaction systems. 33,34 The success and advantages of this method include shorter reaction time, higher yield, higher product purity, improved selectivity, reduced side product formation, and use of milder reaction conditions when compared with conventional heating.…”

Design and synthesis of spiro derivatives containing a thiophene ring and evaluation of their Anti-microbial activity

“…11 1,3-dipolar cycloaddition reactions of azomethineylides has been well developed, and also the reactions proceed with high regio-and stereoselectivity 12,13 . Thiophene and its derivatives are the significant class of heterocyclic compounds possessing broad biological activities, such as antiinflammatory 14 , analgesic 14 , antioxidant 15 , antitubercular, 16 antidepressant, 17 sedative, 18 antiamoebic, 19 oral analgesic, 20 anti-metabolite, 21 and antineoplastic properties. 22 For a extended analysis of the regiochemistry in 1,3-dipolar cycloaddition reaction and also the bioactivity of spiro [pyrrolidine-2,3'-oxindoline] compounds, three varieties of trapping agents like dipolarophiles, diketone, -amino acid, were introduced during this reaction to synthesis a series of spiro [pyrrolidine-2,3'-oxindole] derivatives, with that the bioactivity on anti-microbial activity was evaluated.…”