INTRAMOLECULAR [4+2] CYCLOADDITION IN <I>N</I>-ALLYL- AND <I>N</I>-PROPARGYL-α-FURYL LACTAMS

Authors

  • Дмитрий С. Поплевин RUDN University, 6 Miklukho-Maklaya St., Moscow 117198
  • Евгения В. Никитина RUDN University, 6 Miklukho-Maklaya St., Moscow 117198
  • Владимир П. Зайцев RUDN University, 6 Miklukho-Maklaya St., Moscow 117198
  • Алексей В. Варламов RUDN University, 6 Miklukho-Maklaya St., Moscow 117198
  • Сантош Тильв Goa University, Taleigao Plateau, Goa 403206
  • Фёдор И. Зубков RUDN University, 6 Miklukho-Maklaya St., Moscow 117198

DOI:

https://doi.org/10.1007/4165

Keywords:

epoxyisoindoles, furans, lactams, IMDAF reaction, intramolecular [4 2] cycloaddition

Abstract

The size of nitrogen heterocycle in N-allyl- and N-propargyl-α-furyl lactams, as well as the nature of the unsaturated substituent linked to the nitrogen atom affected the possibility of thermal intramolecular [4+2] cycloaddition between multiple bond and the furan ring. N-Allyl-γ-(α-furyl)butyrolactam was shown to be unreactive at temperatures from 140 to 230°С. Substituted δ-valero- and ε-caprolactams underwent partial Diels–Alder cyclization, forming tautomeric mixtures that contained both the initial open-chain form and the cyclic form (diastereomeric 3a,6-epoxyisoindoles fused with an aza ring) in ratios between 19:81 and 55:45. N-Propargyl-α-furyl lactams did not participate in thermal IMDAF reaction regardless of the ring size and the temperature of the synthesis.

Authors: Dmitry S. Poplevin, Eugeniya V. Nikitina, Vladimir P. Zaytsev, Alexey V. Varlamov, Santosh G. Tilve, Fedor I. Zubkov*

Author Biography

Дмитрий С. Поплевин, RUDN University, 6 Miklukho-Maklaya St., Moscow 117198

Organic Chemistry Department, Faculty of Science, RUDN University, Russia

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Published

2018-06-06

Issue

Vol. 54 No. 4 (2018): Stereoselective synthesis of heterocyclic compounds

Section

Original Papers