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INTRAMOLECULAR DIELS–ALDER REACTION IN THE SYNTHESIS OF 5-ARYLISOXAZOLYLMETHYL- AND 4,5-DICHLOROISOTHIAZOLYLMETHYL-3a,6-EPOXYISOINDOL-3-ONES

Дмитрий Ф. Мерцалов, Лала В. Ловцевич, Евгения Р. Шелухо, Ирина А. Колесник, Сергей К. Петкевич, Владимир И. Поткин, Владимир П. Зайцев
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Abstract


The reaction of 5-arylisoxazolyl- and 4,5-dichloroisothiazolylallylamines with pyromucic acid chlorides (2-furoyl and 5-methyl-2furoyl chlorides) was studied. The reaction proceeds via the initial acylation of the allylamine nitrogen atom and the subsequent spontaneous intramolecular Diels–Alder reaction involving the furan ring of intermediate N-furoylamides with the formation of a single diastereomer of 3a,6-epoxyisoindol-3-ones.

 


Keywords


allylamine; epoxyisoindole; furan; isothiazole; isoxazole; IMDAF reaction; intramolecular [4+2] cycloaddition.

Full Text: PDF (Russian) Supplementary File(s): Supplementary information (812KB)


 

 

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