High-yielding synthesis of deepened cavitands bearing picolyl moieties on the upper rim

Zoltán Nagymihály, L. Kollár

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Conventional high-yielding reactions (such as etherification, condensation reactions) and palladium-catalysed aminocarbonylation served as highly efficient synthetic tools for the synthesis of novel cavitands bearing Schiff-base and carboxamide/2-ketocarboxamide functionalities, respectively. In this way, two families of deepened cavitands with related structures possessing 2-, 3- and 4-picolylamine moieties on the upper rim have been synthesised. Unexpectedly high chemoselectivities towards tetracarboxamides and tetrakis(2-ketocarboxamides) have been observed. The aminocarbonylation of tetraiodocavitand as an iodoaromatic substrate proved to be highly selective in two aspects: (i) no substantial formation of either the mono-, di- or trifunctionalized products was observed and (ii) no 'mixed' products possessing both carboxamide and 2-ketocarboxamide fragments, due to selective simple and double carbon monoxide insertion, were detected.

Original languageEnglish
Pages (from-to)2555-2560
Number of pages6
JournalTetrahedron
Volume71
Issue number17
DOIs
Publication statusPublished - Apr 29 2015

Fingerprint

Bearings (structural)
Condensation reactions
Schiff Bases
Palladium
Carbon Monoxide
Substrates

Keywords

  • Aminocarbonylation
  • Carbon monoxide
  • Carboxamide
  • Cavitand
  • Palladium
  • Schiff base

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

High-yielding synthesis of deepened cavitands bearing picolyl moieties on the upper rim. / Nagymihály, Zoltán; Kollár, L.

In: Tetrahedron, Vol. 71, No. 17, 29.04.2015, p. 2555-2560.

Research output: Contribution to journalArticle

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