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

Authors

  • Дмитрий Ф. Мерцалов RUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russia
  • Лала В. Ловцевич RUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russia
  • Евгения Р. Шелухо RUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russia
  • Ирина А. Колесник Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, 13 Surganova St., Minsk 220072, Belarus
  • Сергей К. Петкевич Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, 13 Surganova St., Minsk 220072, Belarus
  • Владимир И. Поткин Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, 13 Surganova St., Minsk 220072, Belarus
  • Владимир П. Зайцев RUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russia

DOI:

https://doi.org/10.1007/6416

Keywords:

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

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.

 

Author Biography

Владимир П. Зайцев, RUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russia

доцент кафдры органической химии РУДН

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Published

2021-10-21

Issue

Vol. 57 No. 10 (2021)

Section

Original Papers