Reaction of arylmethylidene derivatives of 3H-furan-2-ones with azomethine ylide

Abstract

Previously unknown dispiropyrrolidines were synthesized by 1,3-dipolar cycloaddition of azomethine ylide to 3-arylmethylidene-3Н-furan-2-ones. The cycloaddition reaction was demonstrated to proceed diastereoselectively through an endo-transition state. Alternative transition states for the reaction are discussed.

A Diastereoselective Synthesis of Dispiro[oxindole-cyclohexanone]pyrrolidines by 1,3-Dipolar Cycloaddition

“…The exo -channel ( TS exo ) is not beneficial, because of the repulsion of the cyclohexane core and the oxindole fragment. The results of our control experiment are confirmed by literature data [ 9 , 10 , 11 ]. Under similar conditions, biarylidenecyclohexanones 1a – f ( Scheme 5 ) in the reaction with sarcosine ylide give rise to a mixture of 2 and 3 cycloaddition products at two reactive multiple bonds.…”

“…Up to the present time, a large amount of data has been accumulated on the regio- and stereochemistry for dipolarophiles of different nature, including acrylates, chalcones, and nitrostyrenes, so it is known that ylides generated from sarcosine react regioselectively with the most electrophilic center of the dipolarophile [ 9 , 10 , 11 , 12 , 13 ] (path I , Scheme 1 ) with the formation of endo -adducts in good yields. Exceptions are nitrostyrene, that exhibits a reversed addition selectivity (path II , Scheme 1 ) [ 14 ].…”

Current Trends towards the Synthesis of Bioactive Heterocycles and Natural Products Using 1,3-Dipolar Cycloadditions (1,3-DC) with Azomethine Ylides

“…Proline 1, sarcosine (13), tetrahydroisoquinolinic acid 42, or piperidine-2-carboxylic acid (14) and acenaphthoquinone (33), isatin (2), or indenoquinoxalinone 43 were employed in this cascade protocol to access a variety of biologically important spiroheterocyclic compounds 41 as single diastereoisomers. 24 Regio-and diastereoselective 1,3-DC also afforded dispirooxindolepyrrolidines in a similar way, but employing 3-(arylmethylene)-5-phenyl-3Н-furan-2-ones 44, 25 or 3′-aryl-5′-arylmethylenespiro[2H-indole-3,2′-thiazolidine]-2(1H)4′-diones 45 as dipolarophiles (Scheme 10). 26 Other potential bioactive dispirooxindole derivatives 48 were described by Mondal and co-workers from N-benzylglycine (46) and isatins 2 or acenaphthoquinone (33) with andrographolide (47), isolated from Andrographis panicula- Other α-amino acid derivatives used…”

Synthesis of Compounds of the Pyrimidine Series Based on the Reactions of 3-Arylmethylidenefuran-2(3H)-ones with N,N-Binucleophilic Reagents

“…As a substrate, 3-arylmethylidenefuran-2(3 H )-ones have some advantages. They can be easily obtained, and they are convenient, cost-effective substrates for the synthesis of various hard-to-reach heterocyclic, spirocyclic, and polycyclic compounds [ 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 ]. 3-Arylmethylidenefuran-2(3 H )-ones are substances which combine the properties of internal esters and α,β-unsaturated carbonyl compounds, and they are able to react with substances with mobile hydrogen atoms.…”