Highly regioselective synthesis of glycospiro heterocycles through 1,3-dipolar cycloaddition reaction

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

“…[1][2][3][4][5][6][7] In particular, spiro-and dispiropyrrolidines are important structural entities of many alkaloids and biologically active substances, 8,9 many of which are potential antiviral, anticancer, and anticonvulsant agents. 10,11 5-R-3-arylmethylidene-3H-furan-2-ones may be used as accessible and promising substrates in 1,3-dipolar cycloaddition reactions.…”

2'-[(4-Fluorophenyl)carbonyl]-1'-phenyl-1',2',5',6',7',7a'-hexahydrospiro[indole-3,3'-pyrrolizin]-2(1H)-one

“…Several natural alkaloids and pharmacological agents, contain spiro-oxindole system e.g., spirotryprostatin A, isopteropodine and pteropodine, which have shown important biological activity with potential use in antibacterial, antiprotozoal, and anticancer activities [2]. Spiropyrrolizine oxindoles are important synthetic targets and several reports of such syntheses exist [3,4]. Such new heterocyclic scaffolds can be prepared by the intermolecular 1,3-dipolar cycloaddition reaction of azomethine ylide with olefinic and acetylenic dipolarophiles [5].…”

Stereochemical Aspects of Reaction of 1,3-dipolar Cycloaddition in a Row of Conjugated Enones

“…Кофеин, консерванты, подсластители во всех пробах содержались в пределах допустимых норм. Эффективным способом моделирования типичных гетероциклических систем являются реакции 1,3-диполярного циклоприсоединения [1][2][3]. В качестве диполярофилов широко использовались сопряженные моноеноны и диеноны симметричного строения [4][5][6].…”