AN INTRAMOLECULAR DIELS–ALDER REACTION IN THE SYNTHESIS OF <i>N</i>-AROYL-3a,6-EPOXYISOINDOLE-2-CARBOTHIOAMIDES

Authors

  • Dmitriy F. Mertsalov RUDN University, 6 Miklukho-Maklaya St., Moscow 117198
  • Lala V. Lovtsevich RUDN University, 6 Miklukho-Maklaya St., Moscow 117198
  • Dmitriy M. Shchevnikov RUDN University, 6 Miklukho-Maklaya St., Moscow 117198
  • Yulya M. Dobrushina RUDN University, 6 Miklukho-Maklaya St., Moscow 117198
  • Elena A. Sorokina RUDN University, 6 Miklukho-Maklaya St., Moscow 117198
  • Mikhail S. Grigoriev Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, 31, Build. 4 Leninsky Ave., Moscow 119071
  • Vladimir P. Zaytsev RUDN University, 6 Miklukho-Maklaya St., Moscow 117198 https://orcid.org/0000-0001-9175-7583

Keywords:

allylamine, epoxyisoindole, furfurylamine, isothiocyanate, thiourea, IMDAF reaction, intramolecular [4+2] cycloaddition

Abstract

The reaction of allyl(furfuryl)amines with aroyl isothiocyanates was studied. The reaction proceeded via an initial nucleophilic addition of the allylamine nitrogen atom to isothiocyanates and a subsequent spontaneous intramolecular Diels–Alder reaction involving the furan ring of intermediate N-allyl-N-furfurylthioureas with the formation of a single diastereomer of 3a,6-epoxyisoindoles.

Author Biography

Vladimir P. Zaytsev, RUDN University, 6 Miklukho-Maklaya St., Moscow 117198

доцент кафдры органической химии РУДН

vzaitsev@sci.pfu.edu.ru

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Published

2024-12-13

Issue

Vol. 60 No. 9/10 (2024)

Section

Original Papers