Anthracene-fused isoxazolopyrrolo[2,1-a]isoquinolines via an endocyclic N-acyliminium ion cyclization: A joint experimental and theoretical study

Maria S. Ledovskaya, Alexander P. Molchanov, Rafael R. Kostikov, Taras L. Panikorovsky, Vladislav V. Gurzhiy, Mikhail N. Ryazantsev, Vitali M. Boitsov, Alexander V. Stepakov

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

© 2016 Elsevier Ltd.A simple and efficient strategy is reported for the synthesis of anthracene-fused isoxazolopyrrolo[2,1-a]isoquinolines via an endocyclic N-acyliminium ion cyclization. The cyclization of 18-aryl-21-(2-arylethyl)-22-hydroxy-16-oxa-17,21-diazahexacyclo[6.6.5.315,19.02,7.09,14.015,19]docosa-2,4,6,9,11,13,17-heptaen-20-ones proceeds with high stereoselectivity, leading to 28-aryl-30-oxa-12,29-diazaoctacyclo[13.6.6.32,14.02,14.03,12.04,9.016,21.022,27]triaconta-4,6,8,16,18,20,22,24,26,28-decaen-13-ones. The N-acyliminium cyclization of 18-aryl-21-(2-arylethyl)-20-hydroxy-16-oxa-17,21-diazahexacyclo[6.6.5.315,19.02,7.09,14.015,19]docosa-2,4,6,9,11,13,17-heptaen-22-ones occurs only for substrates with electron-rich aromatic groups in the arylalkyl fragment. In these cases, cyclization also proceeds with a high stereoselectivity with the formation of anthracene-fused isoxazolopyrrolo[2,1-a]isoquinolines as single diastereomers. To understand the mechanisms that allow for cyclization of N-acylimini
Original languageEnglish
Pages (from-to)4827-4834
Number of pages8
JournalTetrahedron
Volume72
Issue number32
DOIs
StatePublished - 2016

Scopus subject areas

  • Chemistry(all)

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