FORMAL [3+3] CYCLOADDITION REACTION OF 4-HYDROXYTHIOCOUMARIN TO 4 Н -CHROMENE-3-CARBALDEHYDES: SYNTHESIS OF THIOCHROMENO[3',4':5,6]PYRANO[2,3- b ]CHROMEN-6-ONES

Ирина А. Семенова; Дмитрий В. Осипов; Юлия В. Попова; Виталий А. Осянин; Олег П. Демидов; Юрий Н. Климочкин

doi:10.1007/5952

FORMAL [3+3] CYCLOADDITION REACTION OF 4-HYDROXYTHIOCOUMARIN TO 4Н-CHROMENE-3-CARBALDEHYDES: SYNTHESIS OF THIOCHROMENO[3',4':5,6]PYRANO[2,3-b]CHROMEN-6-ONES

Ирина А. Семенова, Дмитрий В. Осипов, Юлия В. Попова, Виталий А. Осянин, Олег П. Демидов, Юрий Н. Климочкин

Abstract

A cascade reaction of 4-hydroxythiocoumarin and 4Н-chromene-3-carbaldehydes was developed, consisting of Knoevenagel condensation and oxa-6π electrocyclization in the presence of ammonium acetate as catalyst. A series of polycyclic acetals containing a fused thiocoumarin moiety were obtained.

Keywords

1H-benzo[f]chromene-2-carbaldehydes; 4-hydroxythiocoumarin; 4Н-chromene-3-carbaldehydes; Knoevenagel condensation; formal [3+3] cycloaddition; electrocyclization.

Full Text: PDF (Russian) Open Access

Supplementary File(s): supplementary info (2MB)

Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv

Username
Password
Remember me