an efficient one-pot three-component procedure for the synthesis of new chiral spiro-oxindolopyrrolizidines with highly regio-, diastereo-, and enantioselective from 1,3-dipolar cycloaddition of azomethine ylides and optically pure active cinamoyl oxazolidinone are described. the process occurs at room temperature in aqueous ethanol as green solvent and in the absence of any bidentate chelating...

Cycloaddition reactions represent one of the most powerful processes in organic chemistry. The most common types of cycloaddition reactions are the Diels-Alder (DA) and the 1,3-dipolar cycloaddition reactions (1,3-DCs) which lead to five and six membered rings, respectively. In our ongoing efforts to contribute to the understanding of DA and 1,3-DCs; we studied the following using the B3LYP/6-3...

Using a highly effective binuclear Cu complex as the catalyst, the 1,3-dipolar cycloaddition reactions between 16 alkynes and two azides were successfully performed and resulted in the production of 25 new triazole-containing sorafenib analogs. Several compounds were evaluated as potent antitumor agents. Among them, 4-(4-(4-(3-fluorophenyl)-1H-1,2,3-triazol-1-yl)phenoxy)-N-methylpicolinamide (8...

Drug-like spirocyclic scaffolds have been prepared by fusing fully functionalized pyrrolidine with oxindoles in an approach based on 1,3-dipolar cycloaddition. Reaction between aziridine and 3-ylideneoxindole generated diverse spirooxindole-pyrrolidines in good yield (up to 95%) with high diastereoselectivity (up to >20:1). The reaction also proceeded smoothly with several other synthetically u...

A series of hitherto unreported anthracene-embedded dispirooxindoles has been synthesized via a one-pot three-component 1,3-dipolar cycloaddition reaction of an azomethine ylide, generated in situ from the reaction of isatin and sarcosine to 10-benzylideneanthracen-9(10H)-one as a dipolarophile in 1-butyl-3-methylimidazolium bromide([bmim]Br), an ionic liquid. This reaction proceeded regio- and...

Chiral pyrrolidines and pyrrolizidines with spirooxindole ring systems are the central skeletons for numerous alkaloids and pharmacologically important compounds. Gelesmine, pseudotabersonine, formosanine, isoformosanine, morroniside and mitraphylline are some of the alkaloids containing spirooxindole ring systems. Derivatives of spirooxindole find very wide biological applications as anti micr...

Nitrile oxides were generated by the catalytic dehydrogenation of aromatic aldehyde oximes 2a-g with chloramine-T as oxidizing agent. The 1,3-dipolar cycloaddition of in situ generated nitrile oxides with ethyl oleate 1 produced a series of new ethyl 8-(3-aryl-4-octyl-4,5-dihydroisoxazol-5-yl)octanoate 3a-g in 6584% yield. Some of the synthesized cycloadducts have exhibited moderate to good ant...

The 1,3-dipolar cycloaddition reaction of (E)-7-arylidene-3-(1H-benzotriazol-1-yl)-6,7-dihydroindolizin-8(5H)-one and azomethine ylide which was generated in situ by the 11H-indeno[1,2-b]quinoxalin-11-one L-proline afforded novel 1'-aryl-3”-(1H-benzotriazol-1-yl)-5',5”,6',6”,7',7a'-hexahydro-1'H,8”H-dispiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizine-2',7”-indolizin]-8”-one moderate yields. stru...

Highly efficient fluorous tagging methodology was developed based on catalytic 1,3-dipolar cycloaddition as the key step.